Personalized care for your dog or cat - Kenwood

Highly-rated overnight sitters - Kenwood

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

We planned our trip ahead of time and Bola made sure to keep open communication along the way. As we dropped our pup off to Bola, the transition was very easy. While Bola had Junie, Bola made sure to keep us updated with pictures. Thanks Bola

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Sean O.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$40
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

Cassandra took great care of my dog Ace during his 4-day stay. I can tell he had a good time hanging out with her dog, Chewy. Cassandra was a pleasure to work with and I hope to use her services again for future boarding.

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Joseph G.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

I couldn't have asked for a better family to take care of my puppy while I was traveling. I could tell that the family truly enjoyed taking care of my dog Mac and gave him all the love and cuddles he is used to getting. Liz provided numerous pics and updates every day single day. I will definitely re-book the next time I travel! I would highly recommend Liz and family.

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Katie S.
Sitter Profile Image: Kamiah & Casius D.
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Kamiah & Casius D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
36 reviews
24 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

They took excellent care of my dog. Picture and video were sent to let me know that my dog was doing fine. I will definitely use them again. Great service 👏

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Marjorie L.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was phenomenal!! 5 out of 5 stars doesn’t even begin to cover it. So easy to communicate with, we received more pictures then we knew what to do with, and she was consistently taking the dogs on walks, to the beach, and out for treats. Couldn’t be more thankful. If we are ever in Chicago again we will be using her services!!

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Tony & Victoria B.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
28 reviews
12 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.

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Tiffany S.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was fantastic and our pup clearly loved spending the weekend with her! She took her to play fetch every day and was flexible with us on our return home. 10/10 would recommend!

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Robert M.
Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$45
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60615

Communication with Tiffany was quick and straightforward. She offered to do a meet & greet as early as the same day, which I appreciate. She showed me her space and made Malcolm feel so welcome. She shared pictures and videos while I was away. Even took him to the beach! This was my first experience with Rover and I feel like Ive found my pups forever sitter!

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Anthonisha C.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
135 reviews
28 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

Ann is so great! My pup seemed to love his stay and she was great about sending daily updates and pics. Would definitely book with her again!

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Julian C.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
194 reviews
71 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley and her daughter treated our dog as if she was their own! Regular updates made me feel so confident that she was well taken care of. No issues with the other dogs she had in her care that weekend either. Will definitely book again!!

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Meg B.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara was absolutely amazing with Frankie! From the moment I dropped her off, I could tell she was in safe, caring hands. She kept me updated with regular messages and photos, which really put my mind at ease while I was away. It’s clear she truly loves and understands dogs, and Frankie seemed so happy and comfortable in her care. I couldn’t have asked for a better experience, and I’ll definitely be booking with her again!

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Yahya M.
Sitter Profile Image: Kyla G.
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Kyla G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
68 reviews
29 repeat clients
20 years of experience
West Elsdon, Chicago, IL, 60632

Kyla was the first stranger I’ve ever trusted to keep my Dylan and I am so glad I chose her! She took great care of him while I was away and he warmed up to her instantly. I am very appreciative and will be booking again in the future.

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Dajae R.
Sitter Profile Image: Andre S.
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Andre S.
from
$50
per night
4.7 out of 5 stars
13 reviews
2 repeat clients
8 years of experience
Loop, Chicago, IL, 60605

Andre took amazing care of Howie during his stay!! Andre and his partner sent me updates and made me feel at ease while I was away! I will definitely recommend Andre to anyone!!

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Nadia S.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$53
per night
5.0 out of 5 stars
96 reviews
22 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

Here’s a review you can leave for Jenna on the Rover app: We can't thank Jenna enough for taking such great care of our dog, Lola, while we were away for a family funeral. She went above and beyond, sending us daily pictures and updates that gave us peace of mind during a difficult time. When we missed our flight and needed to extend Lola's stay, Jenna was incredibly accommodating and flexible, which was a huge relief. Lola clearly loved her, and we could tell she was in the best hands. Jenna is sweet, reliable, and a true dog lover. I highly recommend her to anyone looking for a trustworthy and caring dog sitter! We will definitely be using her services again!

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Devina C.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
201 reviews
77 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

Nathan has taken care of our Luna twice now, both times on short notice, and we couldn’t be happier with him. He is incredibly caring, attentive, and truly treats Luna like his own. He kept us feeling completely at ease knowing she was in such good hands. The pickup and drop-off service is an added convenience that we really appreciate. We are so grateful to have found someone we trust and will definitely be using Nathan again in the future. Highly recommend!

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Juhi D.
Sitter Profile Image: Jiayi G.
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Jiayi G.
from
$40
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Jiayi was awesome and I really appreciated all the pics and videos she sent! Perfect person for my firework anxious dog to spend the 4th with. Thank you so much Jiayi!

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Kristine P.
Sitter Profile Image: Tonisa J.
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Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
81 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

Tonisa watched my dog last minute after an emergency when I needed someone the most. She cared for my baby and communicated consistently. I highly recommend her!

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Jenae T.
Sitter Profile Image: Ann-Marie H.
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Ann-Marie H.
Star Sitter
from
$55
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Loved the daily updates with pictures and videos. Made us feel comfy and happy that we booked with you. Also appreciated you taking him out to the dog park, playing with him inside, taking him on walks, and putting him in his crate for nap time/at night. Would book with you again! Thank you so so much for the great care!

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Izzy R.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
24 reviews
18 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Cheyanne was amazing. She had great communication and my dog can be timid and not eat much at dog sitters but she didn't have that problem with her. Best sitter! Thank you

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Nicole M.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
363 reviews
99 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie is so amazing!! So flexible with timing, kind, and sends pictures! She also was so nice in meeting me before so I could make sure my dog would be okay with her dog. Her dog is so chill so it was perfect for my anxious dog. Thank you so much again Katie!!! Definitely will book again 😊😊😊

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Ana H.
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Over 4.1 million
dogs curled up for a sleepover in a sitter's home on Rover1

Cat caregivers near you - Kenwood

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Emmaline H.
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Emmaline H.
from
$14
per visit
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

About: What sets me apart is my long-term experience caring for the same cat for about 8 years, including occasional house sitting. Over that time, I’ve built a strong understanding of her routine, personality, and needs, and focused on keeping her comfortable, safe, and stress-free while her owner is away. I’m dependable, attentive, and respectful of both pets and homes, and I always aim to maintain a calm, familiar environment so cats feel secure in their own space.

Sitter Profile Image: Kayleigh P.
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Kayleigh P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
6 repeat clients
3 years of experience
Hyde Park, Chicago, IL, 60615

Kayleigh was very kind and was amazing with our cat! Our cat has accidents sometimes, but she was able to clean them while we were away. We appreciated her playing with our cat and making sure that she was well taken care of! Thank you!!!

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Minori E.
Sitter Profile Image: Tenzin K.
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Tenzin K.
from
$9
per visit
13 years of experience
Hyde Park, Chicago, IL, 60615

About: I've had a cat myself for 13 years, been a sitter for my neighbor's cat for the past year, and volunteered at Off The Rocks Cat Rescue Shelter for 4 years when I was in college :) Thus, I have extensive experience following detailed instructions to care for cats with the utmost care and responsibility. My cat is also diabetic and I do insulin injections for him, so I am prepared for any special accommodations in caring for your cats!

Sitter Profile Image: Rachel R.
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Rachel R.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
57 reviews
18 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60637

We have a very shy cat but she quickly warmed up to Rachel after a couple visits! Rachel was very good with her and sent lots of adorable photos of her during her visits, which we were so happy to see while we were away on our trip.

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Rheanna B.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
40 reviews
13 repeat clients
10 years of experience
Douglas, Chicago, IL, 60653

Chelsea did an amazing job caring for my kitties over the holidays! First, I ended up booking shorter notice and Chelsea responded immediately, was flexible, and was able to accommodate me and my babies. Chelsea was a great communicator when she was caring for my kitties, she gave consistent updates about how they were doing, as well as the tasks she completed when caring for them (refilling food and water, cleaning the litter box). I really appreciated the time and effort Chelsea put into caring for my babies, especially during the holiday time. Thank you!

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Eden A.
Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$22
per visit
4.9 out of 5 stars
18 reviews
3 repeat clients
7 years of experience
Chicago, IL, 60615

Lucille is an incredibly kind and attentive cat sitter. She made him feel loved and played with him so much. She even took him for a stroll on his backpack. Would highly recommend. Felt like our baby was in wonderful hands!

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Joanna A.
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
47 reviews
17 repeat clients
30 years of experience
Hyde Park, Chicago, IL, 60615

Evan did a wonderful job watching our cat for a long weekend. He was communicative and responsive, which made us feel comfortable and confident that our cat was in great hands.

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Anna B.
Sitter Profile Image: Brianna B.
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Brianna B.
from
$14
per visit
5.0 out of 5 stars
8 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

Brianna was everything you could ask for in a pet sitter! She came like clockwork and made sure our sweet cat had all her needs met. Strong recommendation if you want someone who you know you can trust!

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Bill H.
Sitter Profile Image: Christina D.
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Christina D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
8 reviews
5 repeat clients
10 years of experience
Oakland, Chicago, IL, 60653

I am so happy that I found Christina to take care of my little Rainbow while I was away! She was very caring and they bonded like love at first sight for our meet and greet. It shows that Christina really loves cats and went out of her way to make sure that mine was comfortable and happy! When I came home, everything was neat and clean and Rainbow was happy and ready to play as if I had never left! I would highly recommend Christina and book her again, thank you so much!

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Tracee H.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

As of now I have an aging cat which presents considerable challenges. Tamara was able to provide good care for her as I was away. She has visited my place many times throughout the year and I highly recommend her for all pet care needs. -William

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William P.
Sitter Profile Image: Julia G.
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Julia G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
6 years of experience
Hyde Park, Chicago, IL, 60614

Thank you so much!

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Catherine G.
Sitter Profile Image: Che Maria B.
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Che Maria B.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
25 reviews
7 repeat clients
10 years of experience
Chicago, IL, 60615

Super attentive and responsible. Took great care of Enero!

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Matías Nicolas K.
Sitter Profile Image: Jasmine P.
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Jasmine P.
from
$25
per visit
5.0 out of 5 stars
98 reviews
38 repeat clients
13 years of experience
Kenwood, Chicago, IL, 60615

We’re so lucky to have found Jasmine! I have a very territorial cat but her calm demeanor and patience paid off and he got comfortable with her presence.

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Maya C.
Sitter Profile Image: Amiyah W.
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Amiyah W.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
3 reviews
5 repeat clients
1 year of experience
Grand Boulevard, Chicago, IL, 60615

Amiyah is kind and caring.Glitzy had lots of fun and looked forward to her visits with Amiyah. We felt she was very well cared for and that makes vacationing easier..

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Turqueya W.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
85 reviews
34 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q was professional and seemed to genuinely care for our cat. I mean I'm sure if the cat could talk, he'd say the same thing. We'll definitely use Q again if she's available!

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Kam W.
Sitter Profile Image: Jessy M.
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Jessy M.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
17 reviews
6 repeat clients
13 years of experience
Hyde Park, Chicago, IL, 60615

Jessy was very sweet and attentive with Minou! I appreciated the picture updates and Minou loved her 😄

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Erin F.
Sitter Profile Image: Sally H.
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Sally H.
from
$23
per visit
5.0 out of 5 stars
59 reviews
21 repeat clients
15 years of experience
Kenwood, Chicago, IL, 60653

Sally did drop in visits over Christmas to feed and take care of my cat. She kept me updated on everything and sent me photos with each visit that helped me feel like he was getting great care! I sincerely appreciated her providing care for him while I was gone.

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Claire C.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per visit
4.7 out of 5 stars
12 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60653

Jasmine R was awesome. Thorough and punctual. My kitty was happy and my home was just as I left it. I will use her services again.

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Stacey S.
Sitter Profile Image: Deanna L.
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Deanna L.
from
$14
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
1 year of experience
Kenwood, Chicago, IL, 60615

Deanna took good care of my cat while I was away and kept me updated daily with updates and pictures. She understood that my cat would be nervous due to a very recent move and was very accommodating. Will book again.

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Stephen R.
Sitter Profile Image: Ashleigh P.
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Ashleigh P.
from
$18
per visit
5.0 out of 5 stars
53 reviews
18 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Ashleigh always does a great job and sends detailed updates. It’s always a relief to know Ashleigh will have everything taken care of back at home.

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Lauren P.
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Perfect for high energy dogs - Kenwood

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
128 reviews
58 repeat clients
23 years of experience
Hyde Park, Chicago, IL, 60615

Ashley takes great care of our puppy. Her kids give ample play time to entertain our puppy, and Ashley walks and feeds her well. She also is quick to respond to queries. Our puppy gets excited whenever coming to Ashley’s place.

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Smaida M.
Sitter Profile Image: Bola A.
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Bola A.
from
$49
per day
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

Bola came through for me last minute and took great care of Bea!! She sent me picture updates and communicated well throughout the day. Will definitely be booking again with her.

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Abby B.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

From the moment Teddy entered E. K's home it was like I didn't exist. Kind of like dropping off your kids at preschool and they don't say goodbye. Teddy had a great day with the other dogs especially Allie and will definitely be back.

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Susan L.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$30
per day
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

I was looking for daycare for my dog and am happy to have found Tamara! She’s great with communication and has been flexible which has been very helpful. And my dogs tail is always wagging when we walk up.

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Jennifer C.
Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$30
per day
5.0 out of 5 stars
17 reviews
5 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60615

About: With over two decades of dedicated experience in pet care, I have nurtured and cherished dogs of all ages, from playful puppies to wise elderly companions. My profound joy in this journey stems from the deep connections formed with these furry friends. Having worked with a diverse array of breeds, I've honed my understanding of their unique needs and temperaments. In addition, my expertise extends to puppy training, where patience and consistency are key. Caring for dogs isn't just a passion; it's a lifelong commitment that brings immense fulfillment. I work a full time remote schedule. I am at home Mondays and Fridays. Im off on the weekends. So I have plenty of time to play and go on walks! Your pets can sleep in the room with me on their beds or wherever makes them most comfortable. I have a baby gate or I can also crate your baby if that is what you prefer.

Sitter Profile Image: Tamya O.
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Tamya O.
from
$40
per day
5.0 out of 5 stars
4 reviews
4 years of experience
Woodlawn, Chicago, IL, 60637

Having Tamya provide day care for our Weimaraner MacKenzie was the best decision! We traveled from the DC area to Chicago to visit the new Obama Presidential Library and Center and wanted to ensure she would be in good hands for the several hours we were away. Tamya made planning for MacKenzie very easy and I was impressed with the advanced questionnaire provided so that they could match the needs for her. They got along superbly. Thank you Tamya for caring for our little girl!

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Donna H.
Sitter Profile Image: Torin I.
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Torin I.
from
$43
per day
5.0 out of 5 stars
23 reviews
8 repeat clients
13 years of experience
Grand Boulevard, Chicago, IL, 60615

About: Hi! It's been a pleasure watching so many amazing furry friends over the years here on Rover. I recently got a little buddy myself, so I am focusing on caring for her. If you're a repeat client (I have watched your pet before) feel free to send me a message and I'll see what I can do! Thanks :) currently working week day evenings and some Sundays, but my schedule varies a lot. Feel free to check with me and I’ll let you know what it looks like! My home is completely dog-safe. They won't be able to get into any trouble whether or not I'm around. I think body language is extremely important and I have a knack for figuring out what a dog may be wanting.

Sitter Profile Image: Ebonee A.
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Ebonee A.
from
$45
per day
5.0 out of 5 stars
48 reviews
22 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

I can not say enough about Ebonee! She is totally amazing! She took such good care of Milo and sent pictures and videos of his stay with her. She is responsive and accommodating! I'm am more than pleased with her level of care.

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Marquetta S.
Sitter Profile Image: Quirtina C.
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Quirtina C.
from
$30
per day
16 years of experience
Woodlawn, Chicago, IL, 60637

About: Hi! I’m Quirtina, a lifelong dog lover and dog mom to Biggie, my sweet 5-year-old Cockapoo. I grew up with two dogs, and Biggie is my second personal dog, so I know how much trust it takes to leave your pup in someone else’s care. I also regularly dog sit for friends, and I always aim to make pets feel safe, comfortable, and loved. I’m active and love long walks around Hyde Park, so I’m happy to help with exercise, playtime, cuddles, and keeping your dog’s routine consistent. I have experience with puppies, senior dogs, and administering medications. I’ll pay close attention to your instructions and your dog’s personality, and I’m always glad to send updates and photos for peace of mind. I’m a full time MBA student, so I have plenty of time to care for your pup! I am home most of the time during the day and evening. I live in a secured gated home, with a gated area for quick bathroom breaks outside of regular walks. Your pup will be in safe hands!

Sitter Profile Image: Danielle K.
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Danielle K.
from
$35
per day
5.0 out of 5 stars
11 reviews
2 repeat clients
8 years of experience
Woodlawn, Chicago, IL, 60637

About: I have pet sit all kinds of loving dogs. Since I was 15 My family, friends and neighbors have trusted me to walk, feed, play with and care for their pets. I work full time virtually, so I am flexible and can care for your beloved pups while at home. I only have availability to do overnight boarding on weekends. I have a spacious place for your dog to have plenty of room to play and be comfortable. In addition, I have a dog park and a spacious park/field a walk away from my home. There also is a trail for us to walk as well. I am equipped to feed, walk and sing to your pup.

Sitter Profile Image: Annie X.
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Annie X.
from
$45
per day
4.9 out of 5 stars
157 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

About: ✦Limited spots left for July 4th weekend• South Loop/Downtown Providing calm, personalized care for every pet: Whether it’s in your home or mine, I provide calm, flexible, one-on-one care tailored to each pet’s personality and comfort level. From cozy boarding stays to in-home visits and overnight house sitting, your pets will always be treated with warmth and respect. 📍 Serving Chicago and surrounding suburbs — including Downtown, South Loop, West Loop, Bridgeport, Pilsen, Chinatown, Hyde Park, Lincoln Park, and beyond. Flexible travel options available, with customized arrangements for extended distances. 🐾 My Journey with Purrfect Pet Sit 🐾 Since 2019, I’ve provided trusted, professional pet care for busy Chicago professionals and families. With over six years of experience and many ⭐⭐⭐⭐⭐ reviews, I specialize in creating a stress-free, high-quality experience for both pets and owners. I specialize in cat sitting, small and medium breed, and senior pet care, with experience in administering oral and topical medications. I’m also open to caring for large dogs after a Meet & Greet, to ensure a good fit between each other. 🤝Meet & Greet Policy Meet & Greet is required for all new clients before confirming a booking. This step allows us to review care details, daily routines, home logistics, key access if needed, and overall fit in person, including how your pet and I interact. Scheduling details will be discussed during the inquiry process. 📸💬 Daily Photo & Text Updates You’ll receive regular photo and text updates, so you can travel or work with peace of mind knowing your furry family is happy and safe at my care. I can’t wait to meet your pets and make their time truly Purrfect! 🐾💛 🌞 Schedule & Availability I work full-time with a hybrid schedule in eCommerce, with some days onsite in the western suburb Lombard and others working from home in the city. Because I regularly commute and am comfortable with travel, I’m open to overnight house sittings and extended stays beyond my immediate area when everything is a good fit. 🐾 Drop-in visits: Available early mornings before work and/or evenings after work, depending on location and care needs. Exact visit times cannot be guaranteed, but I always aim to stay within a reasonable time window and will communicate updates as needed. Flexibility is required in terms of visit time. 🏠 House sittings: My standard rate covers overnight care from evenings through mornings and includes standard morning and evening potty walks, plus a final potty break before bedtime. Daytime hours, extended exercise walks, and constant care are not included in the base rate and may require additional fees depending on care needs and scheduling. 🚗Pick-up / Drop-off: Available upon request for repeat clients or when schedules align with my Lombard–Chicago commute route. 🐕 Boarding & daycare: Limited spots available - please message to confirm availability. 🏡 Home Environment & Safety Calm, cozy home with fenced yard and pet-friendly setup - a safe, peaceful space for every guest to relax, play, and rest comfortably during their stay.

Sitter Profile Image: Kyle H.
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Kyle H.
from
$40
per day
5.0 out of 5 stars
28 reviews
6 repeat clients
22 years of experience
Hyde Park, Chicago, IL, 60615

About: Kyle and Ben have been caring for dogs in our home for over fifteen years. We have experience administering medications, whether they be topical, ingested or intravenous. Our goal is to make sure you know your dog is safe and well cared for while you're out of town. We are very quick to respond to all phone calls, text messages and emails and will keep you posted with photos and updates on how your dog is doing while they are staying with us. We also provide flexible pick up and drop off hours for your convenience and can provide transportation if necessary. Kyle has several years of experience working in the pet care industry, starting with shelter work, moving onto a dog daycare/boarding facility and managing of two different dog and cat supply stores (one local, one corporate) in the last fifteen years. She is certified in dog and cat first aid and CPR by the American Red Cross and has experience administering topical, oral and intravenous medications. She has extensive experience handling senior and disabled animals, as well as dogs with behavioral issues. We have always loved dogs and owned dogs throughout our respective childhoods, but Kyle has gotten more hands on experience in the last fifteen years by dabbling in different fields of animal care. She worked as a kennel attendant at the local SPCA for a period of time, caring for homeless dogs, cats and rabbits. It was there that she learned proper care techniques and how to administer medications. She took these skills with her when she went to work first as a kennel attendant and then as the office manager of a small dog daycare and boarding facility. She spent the next seven years serving as store manager of two different natural dog and cat supply stores, where she helped pet owners provide their animals with healthy natural foods, treats and other supplies. She also organized many in store events to help highlight and raise funds for many local rescues and shelters. In 2020, Kyle completed school to become a dog groomer and has been grooming dogs in Hyde Park for the last several years. Both Kyle and Ben work mainly from home, or not far from home. Kyle works as a dog groomer and is able to bring your dog to work with her during the day to minimize any time your dog may spend without human supervision. We never allow anyone off leash on walks, and we do not utilize off leash dog parks for safety reasons. All of our pets are fully vaccinated. Feeding times are always supervised to prevent any potential food aggression. Toys and chews are put away when human supervision is unavailable to prevent resource guarding.

Sitter Profile Image: Jane C.
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Jane C.
from
$33
per day
5.0 out of 5 stars
1 review
10 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve cared for my sweet girl for about 10 years now. She’s changed over the years from a newly adopted young shelter dog to a senior dog and I’ve consistently modified how I care for her to meet her needs. I have boarded many family dogs too from tiny multi poms to larger sweet pits. I really feel at home with animals and treat every dog with patience and care like my own girl. I work from home, live across the street from a big park, and can offer plenty of walks, attention, and playtime. Please be sure to share If you’re dog requires supplements, medication, special feeding schedules/protocols, behavioral things I should be mindful of. I work from home Monday thru Friday. Typically up with my dog by 6. She gets a long walk in the am and after work. Plenty of walks in between work for potty breaks. Each day can look different though based on weather and overall energy level of your dog. I can adjust your dogs needs when it comes to feeding schedule, affection, attention, and stimulation. I vary my techniques based on your dog’s personality and what they need when it comes to affection, space and activity level. I am flexible!

Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per day
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Timothy is our puppy’s favorite sitter (and ours too!). It’s clear he really understands and empathizes with dogs of all ages and sizes. We’ve had multiple stays at Timothy’s place, and every time our dog comes home happy, well-cared for and occasionally having made new dog friends! We especially appreciate the way he handles our rambunctious labrador puppy- calm, kind, and confident. It’s such a relief knowing she’s in good hands. We’re grateful to have found him, highly recommend!

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Eric F. R.
Sitter Profile Image: Monique O.
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Monique O.
from
$50
per day
5.0 out of 5 stars
4 reviews
25 years of experience
Woodlawn, Chicago, IL, 60637

About: I have taken care of dogs my entire life , I was a baby who grew up with a Irish Setter. and so my life's journey has been traveled with My best buddies . My family and my pets. Their love and kindness cannot be measured and they deserve the very best of care. I pride myself on training tips and methods i have used on puppies to older dogs i’ve taught behavior adjustments. I believe a healthy fit pup is a happy one . I was also involved in a program we called visiting buddies , taking puppies to spend time with senior citizens and pre school students. throughly enjoyed by everyone involved. I am currently working part time and my schedule is flexible, I work in events. my availability is after 12 for walking and boarding generally but with enough notice I can work some morning hours. I have a large fenced yard as well as a dog run on the side of our home. I have a very friendly furry baby who will give your pup hours of entertainment. I you. would prefer. your pup was crated I. have a very large kennel indoors as well as outside. My home has tons of space .

Sitter Profile Image: Gabriel V.
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Gabriel V.
from
$33
per day
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Bridgeport, Chicago, IL, 60608

Gabriel was an excellent dog sitter for Walnut. He was attentive, patient, and very professional throughout the entire experience. He communicated clearly, provided updates, and always confirmed details, which gave me great peace of mind. Walnut seemed very happy and comfortable with him, and it was clear he genuinely enjoyed spending time with Gabriel. I truly felt that Walnut was in good hands. I would definitely recommend Gabriel and would love for him to continue sitting for us in the future.

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Mina R.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$45
per day
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was absolutely fabulous with my boy! Took him for a nice long walk. I could tell when I picked him up that he had really bonded with her.

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Isabel C.
Sitter Profile Image: Monica M.
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Monica M.
from
$35
per day
5.0 out of 5 stars
14 reviews
5 repeat clients
19 years of experience
Bridgeport, Chicago, IL, 60608

About: Hi! My name is Monica and I recently graduated from Indiana University. I’ve grown up around animals my entire life, so caring for them has always come naturally to me. While I was in college, I fostered through local animal shelters, which gave me experience caring for animals with all different personalities, ages, and needs. I’m also currently a volunteer at the Anti-Cruelty Society in Chicago, where I help care for animals and support the shelter. I work from home, so I’m able to give pets a lot of attention throughout the day. Your pet will never be left alone for long. My dad is also recently retired and home most of the time, so there’s always someone around to give extra attention, playtime, and care. I have a small Yorkie named Tucker and a cat named Penny. They’re both very friendly and used to being around other animals. Tucker is great at matching other dogs’ energy (whether they want to play or relax), and Penny is very calm and tends to mind her own business. Whether it’s walks, playtime, feeding, or just keeping your pet company, I treat every animal like they’re part of the family. I’d love the opportunity to care for your pet and make sure they feel safe, happy, and comfortable while you’re away! I recently graduated from Indiana University and am now back home in Chicago full-time. My dad is retired and home all day, and I spend most of my time at home too, so your pet will always have company and attention. I’m not super busy and genuinely love being around animals — it’s the perfect setup! I have a private, fully fenced yard and never let pets outside without supervision. My home is spacious, and pets are welcome to relax anywhere they’d like. I also have a 2-year-old, 4.5-pound Yorkie who mostly keeps to himself but is always up for a little playtime if your pet wants a buddy! I’m happy to crate your dog at night if you prefer, or they’re welcome to sleep with me — I’d love that too!

Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per day
5.0 out of 5 stars
28 reviews
12 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

About: Looking for a dog sitter with a passion for pups and years of experience? I’ve not only been a dog mom for 14 years, but recently assisting in training the now 6 month old puppy that’s in my parent’s care. I’m the #1 dog sitter amongst my network, not only because I work from home and have availability, but because I also include their fur babies in my dog’s activities as well i.e. dog park dates, dog birthday parties, and doggie brunch! I’m a full- time remote employee with a very relaxed work schedule. Your pet will be spending the majority of their time in my care. I have a fenced front yard and a patio along with one 22lbs dog that will keep your pet company. I also have a lot of space to allow the dog to move around as they would like.

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Adventure-ready dog walkers - Kenwood

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara has been walking my dog Blowe daily since this summer, and I honestly couldn’t ask for better care. Blowe genuinely looks forward to his morning walks with her and always comes back happy and relaxed. Having someone I trust with him every day gives me real peace of mind.

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Al T.
Sitter Profile Image: Emmaline H.
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Emmaline H.
from
$18
per walk
1 repeat client
10 years of experience
Hyde Park, Chicago, IL, 60615

About: What sets me apart is my focus on individualized care for each pet. I take time to understand their routine, personality, and comfort needs so they feel safe and relaxed while you're away. I’m reliable, attentive, and make communication a priority by providing regular updates with photos and messages. Pet care fits easily into my daily routine because I have a flexible and organized schedule that allows me to prioritize visits, feedings, and check-ins consistently. I’m able to plan my day around morning, afternoon, and evening care as needed, making sure pets receive attention on time and without rush. I’m also good at managing responsibilities, so I can balance pet care with other commitments while still being reliable and responsive. Whether it’s drop-ins, feeding, playtime, or house sitting, I can adapt my routine to meet each pet’s needs and ensure they stay comfortable and well cared for throughout the day. I provide care for pets in their own home to help keep them comfortable in their familiar environment. I offer house sitting, where I stay in the home as needed to provide companionship, maintain routines, and make sure pets are fed, walked, and well cared for. I also offer dog walking and daily walks to ensure pets get regular exercise, bathroom breaks, and attention throughout the day. In addition, I can handle scheduled feedings and basic care routines exactly as instructed by the owner. I do want to note that I do not offer boarding or training services. My focus is on in-home care and walking services, making sure pets stay safe, relaxed, and well looked after while their owners are away or busy.

Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: artiss m.
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artiss m.
from
$15
per walk
20 years of experience
Chicago, IL, 60615

About: Animals have been a part of my life for as long as I can remember. I grew up surrounded by dogs of all sizes and breeds, from a beloved Cocker Spaniel to two Giant Schnauzers and later a Pit Bull. Each one helped shape my love and understanding of animals and taught me how unique every pet’s personality can be. Today, I’m the proud owner of a French Bulldog who keeps me on my toes and a pet snake, giving me experience caring for both traditional and exotic pets. I’ve also spent time around cats through friends and family and am comfortable caring for feline companions as well. While attending Ball State University, I volunteered at local animal shelters, helping care for animals and supporting their daily needs. Whether your pet is energetic, shy, playful, or senior, I understand the importance of providing patience, attention, and loving care. I treat every animal as if they were my own and strive to make them feel safe, happy, and loved while you’re away. Pet care is already a part of my daily routine, as I currently care for my own pets and understand the importance of consistency, attention, and reliability. I work as a State Farm agent in Chicago’s West Loop, and because it is a family-owned business that my family manages and operates daily, I have some flexibility within my schedule when needed. During the week, I am available for pet care before work, after work, and during my lunch break. Depending on the day and my workload, I may also have additional flexibility to accommodate specific care needs. On weekends, I typically have more availability and can provide extra time and attention for walks, drop-in visits, overnight care, and companionship. I am careful not to overbook myself because I believe every pet deserves quality care and attention. When I accept a booking, you can trust that I have the time and availability to provide dependable, attentive care and ensure your pet remains safe, comfortable, and happy while you’re away. At this time, I’m unable to offer boarding services in my home due to my own pets. However, I am happy to provide a variety of other services, including drop-in visits, dog walking, overnight stays, and personalized in-home pet care. My goal is to ensure your pets remain comfortable in their familiar environment while receiving the attention, companionship, and care they deserve. Whether your pet needs playtime, feeding, medication administration, exercise, or simply a reassuring presence while you’re away, I am committed to providing safe, reliable, and compassionate care tailored to their needs.

Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
18 reviews
3 repeat clients
5 years of experience
Hyde Park, Chicago, IL, 60615

Thank you for giving Kaia lots of pets and cuddles!! We appreciate it!!!

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NORMA L.
Sitter Profile Image: Brianna B.
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Brianna B.
from
$15
per walk
5.0 out of 5 stars
8 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

My boy seemed happy in every photo. She took great care to keep me updated before and after every walk. She even cleaned him up after an accident. I would definitely book with her again!

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Nicole H.
Sitter Profile Image: Amiyah W.
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Amiyah W.
Star Sitter
from
$10
per walk
5.0 out of 5 stars
3 reviews
5 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

About: I've had pets since I was 9. From 9 till now I've had cats, dogs, fishes, and guinea pigs. I have experience with dealing with pets that may have previously trauma issues also with pets that may need careful care like medince or special needs. Even pets that don't need extra care just pets that wants to have long walks or need a lot of play time . Pet care is an important part of my routine, and I make sure I have dedicated time each day to give every pet the attention and care they deserve. I plan my schedule around my bookings so I can be reliable, on time, and fully present for walks, feedings, playtime, potty breaks, and companionship. I believe consistency is important for pets, so I do my best to maintain their normal routine and provide dependable, loving care. I provide a safe, clean, and caring environment for every pet. I follow each pet’s normal routine as closely as possible, including feeding schedules, fresh water, walks, playtime, potty breaks, and any medications if needed. I also make sure pets receive plenty of attention, affection, and exercise based on their individual needs and energy level. When caring for pets in a client’s home, I respect their space, keep the home clean, follow all care instructions carefully, and send regular photo and text updates so owners know their pets are happy and well cared for. My goal is to make every pet feel comfortable, secure, and loved while their family is away.

Sitter Profile Image: Julia G.
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Julia G.
Star Sitter
from
$14
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
6 years of experience
Hyde Park, Chicago, IL, 60614

Julia was absolutely wonderful with my pooch! My pup took to her right away. She was very communicative and flexible with accommodating my last minute requests. And with each walk I received pics and my pup couldn’t have looked happier! 😊

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Jasmyn M.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
85 reviews
34 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q was great with Remi! She showed up ready to walk him and was prepared with any questions she had.

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Abi S.
Sitter Profile Image: Che Maria B.
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Che Maria B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
25 reviews
7 repeat clients
10 years of experience
Chicago, IL, 60615

She was great with my dogs who are shy at first. She gave me some great feedback and tips for walking my dogs and even came out in awful weather. Highly recommend!

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Julie G.
Sitter Profile Image: Andrea W.
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Andrea W.
from
$19
per walk
6 years of experience
Kenwood, Chicago, IL, 60615

About: I am experienced in very detailed pet care instructions and understand that those pets have unique needs. I have experience with administering medical supplements, adhering to specific feeding schedules and portion requirements. I have followed individualized activity plans and routines for both dogs and cats. I want to provide the consistency in a pets routine while their owners are away. I promote owner-established potty training methods in regards to 6 months and older potty training behaviors. My approach combines reliability, patience, and genuine affection for animals while providing pet owners with confidence that their pets are receiving attentive and compassionate care in their absence. I am a Retired NCAA WBB coach so I have time to care for your fur family! I Can adjust to your pets favorite routine! I stay in your home so that your fur family is in their most safe space! I stick to their routines and routes! I can include new enrichment activities and stick to what works for them! I understand crating and routine! I have also slept w 4 animals in bed so that were very supported during the owner’s mini vacation.

Sitter Profile Image: Bola A.
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Bola A.
from
$30
per walk
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

One of the best I’ve experienced on this app so far. Bola was very effective, communicative and a joy to work with! Django loves her so much! I highly recommend her for your pet!

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Johnathan M.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per walk
4.7 out of 5 stars
12 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60653

Consistent, punctual, communicative, and generous. She shows up everyday in a timely manner, cares for my dog, and even gives complementary baths and cleaning if she makes a mess. HIGHLY RECOMMENDED 🤗 she offers a good range of services as well!!

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Nyla S.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

About: I’ve loved animals since I was a kid. My many years of pet ownership has trained me for this opportunity. My Chewy is both happy and healthy. I’m recently retired. My daily schedule is built around the needs of my boy, Chewy. He’s walked at minimum three (3) times a day; my friends and family know the routine. I have a secure deck to allow fresh air and free movement with guaranteed security. I have a crate if needed, but think all dogs should have free movement daily.

Sitter Profile Image: Ashleigh P.
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Ashleigh P.
from
$19
per walk
5.0 out of 5 stars
53 reviews
18 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Ashleigh did a great job with our girl Mabel! Mabel’s new to the family and still adjusting and Ashleigh put my mind at ease while I was away for the weekend.

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Amy-Jane B.
Sitter Profile Image: Valeria V.
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Valeria V.
from
$17
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Val is great with our old soul! She is punctual, leaves great notes, and our dog looks forward to time with her.

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Allecia H.
Sitter Profile Image: Morgan P.
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Morgan P.
from
$16
per walk
5.0 out of 5 stars
20 reviews
3 repeat clients
14 years of experience
Grand Boulevard, Chicago, IL, 60653

Morgan does a great job with my pup. Very professional and my dog loves her.

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Michelle R.
Sitter Profile Image: Karissa L.
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Karissa L.
from
$25
per walk
4.9 out of 5 stars
19 reviews
7 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60615

Our dog took an instant liking to Karissa—unusual for him—and is always very excited to see her. She has always arrived right on time, and it has been a pleasure interacting with her. We highly recommend her!

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Eric D.
Sitter Profile Image: Huibo L.
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Huibo L.
from
$19
per walk
1 repeat client
10 years of experience
Chicago, IL, 60615

About: I’ve taken care of my own dog and cat for 7 years and before then was the go to sitter for all my friends with pets! I’m also a PhD student in psychology working in animal behaviors. Since young, I understand animals and respect them: how we treat them influences their behaviors. I’ve got the heart and the training to give your babies the best care they deserve when you are away! My schedule is flexible as long as we communicate in advance. Mornings work the best at the moment but let me know what you need I’ll try to make it work :) I have a comfy apartment with one dog and one cat. They’ll keep your baby company if you board with us. I’m skilled in introducing new animals to each other, I try to adjust to each animals temperaments. On other visits I try to get to your babies first as well, and of course your tips are always appreciated as you know them the best!

Sitter Profile Image: Lisa "Rane" B.
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Lisa "Rane" B.
from
$30
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
25 years of experience
Kenwood, Chicago, IL, 60615

Lisa "Rane" was fantastic with Bobby. She is prompt and personable. My dog received her well upon their first meeting. She and I developed a good rapport which led me to feel comfortable trusting her with Bobby. I will make her my first request when needing your service in the future.

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Barbara B.
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Large dog specialists near you - Kenwood

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

We planned our trip ahead of time and Bola made sure to keep open communication along the way. As we dropped our pup off to Bola, the transition was very easy. While Bola had Junie, Bola made sure to keep us updated with pictures. Thanks Bola

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Sean O.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

I couldn't have asked for a better family to take care of my puppy while I was traveling. I could tell that the family truly enjoyed taking care of my dog Mac and gave him all the love and cuddles he is used to getting. Liz provided numerous pics and updates every day single day. I will definitely re-book the next time I travel! I would highly recommend Liz and family.

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Katie S.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was phenomenal!! 5 out of 5 stars doesn’t even begin to cover it. So easy to communicate with, we received more pictures then we knew what to do with, and she was consistently taking the dogs on walks, to the beach, and out for treats. Couldn’t be more thankful. If we are ever in Chicago again we will be using her services!!

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Tony & Victoria B.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was fantastic and our pup clearly loved spending the weekend with her! She took her to play fetch every day and was flexible with us on our return home. 10/10 would recommend!

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Robert M.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
194 reviews
71 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley and her daughter treated our dog as if she was their own! Regular updates made me feel so confident that she was well taken care of. No issues with the other dogs she had in her care that weekend either. Will definitely book again!!

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Meg B.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara was absolutely amazing with Frankie! From the moment I dropped her off, I could tell she was in safe, caring hands. She kept me updated with regular messages and photos, which really put my mind at ease while I was away. It’s clear she truly loves and understands dogs, and Frankie seemed so happy and comfortable in her care. I couldn’t have asked for a better experience, and I’ll definitely be booking with her again!

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Yahya M.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$53
per night
5.0 out of 5 stars
96 reviews
22 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

Here’s a review you can leave for Jenna on the Rover app: We can't thank Jenna enough for taking such great care of our dog, Lola, while we were away for a family funeral. She went above and beyond, sending us daily pictures and updates that gave us peace of mind during a difficult time. When we missed our flight and needed to extend Lola's stay, Jenna was incredibly accommodating and flexible, which was a huge relief. Lola clearly loved her, and we could tell she was in the best hands. Jenna is sweet, reliable, and a true dog lover. I highly recommend her to anyone looking for a trustworthy and caring dog sitter! We will definitely be using her services again!

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Devina C.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
201 reviews
77 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

Nathan has taken care of our Luna twice now, both times on short notice, and we couldn’t be happier with him. He is incredibly caring, attentive, and truly treats Luna like his own. He kept us feeling completely at ease knowing she was in such good hands. The pickup and drop-off service is an added convenience that we really appreciate. We are so grateful to have found someone we trust and will definitely be using Nathan again in the future. Highly recommend!

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Juhi D.
Sitter Profile Image: Jiayi G.
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Jiayi G.
from
$40
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Jiayi was awesome and I really appreciated all the pics and videos she sent! Perfect person for my firework anxious dog to spend the 4th with. Thank you so much Jiayi!

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Kristine P.
Sitter Profile Image: Tonisa J.
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Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
81 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

Tonisa watched my dog last minute after an emergency when I needed someone the most. She cared for my baby and communicated consistently. I highly recommend her!

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Jenae T.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
363 reviews
99 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie is so amazing!! So flexible with timing, kind, and sends pictures! She also was so nice in meeting me before so I could make sure my dog would be okay with her dog. Her dog is so chill so it was perfect for my anxious dog. Thank you so much again Katie!!! Definitely will book again 😊😊😊

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Ana H.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Tim is a great guy who is amazing with animals. He provided pictures and updates every day. My dog did not even want to leave. He obviously provided great care and was very flexible with my schedule for pick up and drop off. I really appreciate his dedication and genuine love of animals.

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Daniel G.
Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
128 reviews
58 repeat clients
23 years of experience
Hyde Park, Chicago, IL, 60615

Great host. Very communicative and friendly. They took my 100 pound dog Blu with same day notice which of course can be hard to do, so I'm grateful. They also kept me updated with pics & vids and any special moments of attention throughout the entire stay. They're very good about taking him out too for potty breaks, which is important for a big dog especially. Blu was clean and happy when he left and we will definitely use them again. Thank you again for your help!

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Del S.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
53 reviews
10 repeat clients
21 years of experience
Bridgeport, Chicago, IL, 60616

Sarah B was so nice and accommodating. This is the first time my pet has stayed with a sitter and my mind was completely at ease. Thanks Sarah!

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Anne S.
Sitter Profile Image: Dominique F.
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Dominique F.
from
$43
per night
4.6 out of 5 stars
73 reviews
39 repeat clients
16 years of experience
South Shore, Chicago, IL, 60637

I am very particular about who I let be around my fur babies so finding Dominique was heaven sent! She’s amazing and does well with handling both of my pits who I know have tons of energy! I appreciate her a lot!

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Calia B.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$58
per night
5.0 out of 5 stars
49 reviews
20 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Steven was great! He has a calm disposition and Jessy loved him. He took her on a walk and played fetch and kept me updated with photos! Would definitely use him again.

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Rachel A.
Sitter Profile Image: Christina L.
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Christina L.
from
$55
per night
5.0 out of 5 stars
63 reviews
21 repeat clients
15 years of experience
West Town, Chicago, IL, 60622

Amazing sitter for our dog! This was our first time leaving her for so many days not with family. Christina was great about sending updates and took wonderful care of Gobi. Will absolutely book with her again!!

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Pranshul G.
Sitter Profile Image: Shani M.
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Shani M.
Star Sitter
from
$42
per night
5.0 out of 5 stars
16 reviews
9 repeat clients
15 years of experience
Roseland, Chicago, IL, 60628

Shani was so great! This was our first time leaving our dog Lucy and Shani made us feel comfortable providing daily updates with photos and videos. Lucy loved being at her home and we will definitely return!

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Allie R.
Sitter Profile Image: Angel V.
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Angel V.
Star Sitter
from
$47
per night
5.0 out of 5 stars
111 reviews
30 repeat clients
15 years of experience
Humboldt Park, Chicago, IL, 60624

He went above and beyond what I expected. The retractable leash broke so he bought another 1. He didn't have to do that but he did. Always sent me photos daily. Highly would recommend Angel.

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Matt L.
Sitter Profile Image: Manuel P.
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Manuel P.
from
$40
per night
4.9 out of 5 stars
48 reviews
16 repeat clients
8 years of experience
West Lawn, Chicago, IL, 60629

Manuel was so good to my baby Luna!!! He agreed to a last minute booking for me during a week long vacation. He sent daily photos and updates and was very responsive to messages throughout her stay. We will DEFINITELY book with him again!

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Pascale L.
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