Personalized care for your dog or cat - Woodlawn

Highly-rated overnight sitters - Woodlawn

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: 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: 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: 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: Dwight C.
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Dwight C.
Star Sitter
from
$30
per night
5.0 out of 5 stars
225 reviews
92 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

Dwight is amazing with Cooper. He'll be my go-to sitter whenever I need one! He sends great update texts and pics and seems to really care about the dogs he sits watches. He also has a sweet dog and cat himself.

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Ariel J.
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: 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: 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: 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: 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: 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: Victoria A.
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Victoria A.
from
$40
per night
5.0 out of 5 stars
11 reviews
6 repeat clients
16 years of experience
Englewood, Chicago IL, IL, 60621

My Gizelle walked right into Victoria's place inspecting every corner before Victoria could give her a proper greeting! Gizelle was very comfortable and tool to Victoria who sent photos throughout the days I was gone. Somehow Victoria got Gizelle to use a pee pad and play with a toy. Things she never does at home. I am grateful for Victoria's care. Thank you!

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Tracye 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: Janet C.
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Janet C.
Star Sitter
from
$47
per night
5.0 out of 5 stars
85 reviews
40 repeat clients
30 years of experience
Beverly, chicago, IL, 60655

My dog Buddy had the best of time with Janet. I would highly recommend Janet. Buddy was almost sad returning home. I received pictures during the stay which I really loved. Thank you Janet for making my dog feel at home and loved!

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Birgitte D.
Sitter Profile Image: Ra'eesa S.
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Ra'eesa S.
from
$45
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

Ra'eesa kept our doggy while we were out of town. I didn't have to worry about him. He was in good hands with her. She is so nice! She sent pics and videos. Will definitely use her again.

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Andrea R.
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: Quirtina C.
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Quirtina C.
from
$38
per night
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: 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.
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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 - Woodlawn

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

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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: 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: Claire P.
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Claire P.
from
$16
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

Communicated so well and was super kind! Very responsive and helpful!

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Vanessa C.
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: 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: 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: Coretta S.
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Coretta S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
289 reviews
102 repeat clients
3 years of experience
South Shore, Chicago, IL, 60649

Coretta is awesome!! She dropped in on my fur babies twice a day while I was away. She sent a detailed summary and photos after each visit. She followed all instructions regarding their feeding and medication, as well as instructions regarding opening/closing the blinds and activating the echo dot each day to give them some background noise. I can be a little overprotective of my kitties, but I was able to enjoy my trip because I felt confident that she was taking care of them!!

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Devyn C.
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: 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: 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: Manuela G.
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Manuela G.
from
$11
per visit
5.0 out of 5 stars
28 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, IL, 60637

So easy, good communication,

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Frances P.
Sitter Profile Image: Kristen M.
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Kristen M.
from
$16
per visit
10 years of experience
Hyde Park, Chicago, IL, 60637

About: I’ve been around cats all my life and have a deep love for them! No matter their personality I can adapt to their needs and make them feel safe and happy!

Sitter Profile Image: Maia S.
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Maia S.
from
$14
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Hyde Park, Chicago, IL, 60637

She did an amazing job with my two cats on a last minute request, my boys were very well taken care of.

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Scott B.
Sitter Profile Image: Huibo L.
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Huibo L.
from
$15
per visit
1 repeat client
8 years of experience
Chicago, IL, 60615

About: My cat Clove (he goes by Miantiao, which means noodle, at home much more) knows how to high five and answers to his name. Cats are smart enough to be trained if you know how to do it and treat them right! I’m here to give them the best care they deserve when you are away :)

Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$23
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

Rebecca was an absolute dream. I got awesome updates and videos of my kitty having both playtime and snuggles. She was flexible, responsive, and my cat clearly had fun with her. I was so relieved to know that he was well cared for while I was away.

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Veronica C.
Sitter Profile Image: Zoe E.
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Zoe E.
from
$14
per visit
5.0 out of 5 stars
2 reviews
4 years of experience
Hyde Park, Chicago, IL, 60637

Zoe was so great! My dog is a nervous rescue and she was super understanding and did everything possible to accommodate.

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Che Maria B.
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.
Sitter Profile Image: Leah C.
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Leah C.
from
$23
per visit
4.9 out of 5 stars
13 reviews
3 repeat clients
11 years of experience
Woodlawn, Chicago, IL, 60637

Leah was great! Came in clutch on short notice.

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Jarron W.
Sitter Profile Image: Rachel M.
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Rachel M.
from
$17
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
30 years of experience
Chicago, IL, 60637

This was our third time booking with Rachel - she is so great with our cats! She’s very responsive and we always know that our kitties are in good hands.

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Ivy Y.
Sitter Profile Image: Dominique L.
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Dominique L.
from
$23
per visit
4.9 out of 5 stars
47 reviews
21 repeat clients
5 years of experience
Woodlawn, Chicago, IL, 60637

Dominique went above and beyond while caring for Scally. It was not as easy because of some major hiccups, but Dominique was absolutely willing to do whatever necessary to provide excellent care for Scally. I would absolutely ask her back to care for Scally. Anyone would be lucky to hire her to care for their pets.

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Shannon M.
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Perfect for high energy dogs - Woodlawn

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: 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: 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: 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 did such a great job with our 5 month old puppy! She made sure Connie felt safe and comfortable during one of our first times away from her, and Connie returned home tuckered out from a great day of play.

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Kelsie L.
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: 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: Dwight C.
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Dwight C.
Star Sitter
from
$18
per day
5.0 out of 5 stars
225 reviews
92 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

This was our first time using Rover, so we were a bit nervous about leaving our two pups for the day (especially a teething puppy). Dwight however made us feel at ease and we appreciated that he sent us several pictures throughout the few hours our pups were with him. He even gave our pups a new toy! Thanks Dwight !

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Kai N.
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: 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: Agustina P.
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Agustina P.
from
$60
per day
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I have extensive pet care experience that began in my childhood. Growing up, I was responsible for a variety of pets, including dogs, cats, and small mammals. This early exposure taught me the essentials of animal care, from feeding and grooming to understanding their behaviors and health needs. Over the years, I have honed my skills in providing attentive and compassionate care, ensuring that each pet feels loved and well-tended. This lifelong passion has equipped me with the knowledge and empathy necessary to handle a wide range of pet care responsibilities confidently. I work from home and I am a home body except when I walk outdoors, run or bike! A walk is so much better with a dog I have plenty of space for dogs to run as I has a long hallway and a downstairs! I have parks 2 blocks down where I live and a dog area.

Sitter Profile Image: Dominique F.
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Dominique F.
from
$40
per day
4.6 out of 5 stars
73 reviews
39 repeat clients
16 years of experience
South Shore, Chicago, IL, 60637

About: Hi I'm Dominique, here to get out and walk Dogs or just be a friendly companion for your pets. I understand deeply the responsibility of careing for and loving our furry friends. What's better than knowing your furry friend is happy and healthy especially after being back from a busy day, or just knowing someone is there to help when your just not feeling good! That someone is me! I couldn't have found a better Gig! All animals deserve the attention they desire! They deserve to live a good life and get fresh air. I'll be there as a helping hand so please be detailed as possible with your pets individual needs and I assure a great visit. I'm a full time worker for rover, I have a 1 bed apartment in Pilsen very dog friendly neighborhood. I am available so contact me 😊 thank you. I have been caring for animals my whole life I have their best interest. Thanks for choosing river I am available full time. Contact me anytime! Im currently working part time so I have plenty of time to care for your pets, it would be my pleasure! Contact me for bookings! I have a fenced yard and other friendly pets to keep your dog company I also have a crate and for your pup if needed and plenty of space in my house.

Sitter Profile Image: Alexis W.
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Alexis W.
Star Sitter
from
$80
per day
5.0 out of 5 stars
29 reviews
8 repeat clients
5 years of experience
South Shore, Chicago, IL, 60637

About: I give animals good eye contact, effective tone, pay attention to their physical capabilities, and show love, respect, and observe surroundings for danger while walking I am normally home early mornings and during the day. Some days I work events as an artist but I have a very flexible schedule. I make sure the floors are clear so that animals are free to roam. I don’t keep chemicals or certain plants out that would harm animals.

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: 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: 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: 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: Nakeisha B.
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Nakeisha B.
from
$35
per day
4.8 out of 5 stars
65 reviews
25 repeat clients
10 years of experience
Grand Crossing, Chicago, IL, 60619

We left our 7 month old for a day while we hit the lakefront, and he seemed to have loved his stay! Nakeisha sent us updates throughout the day, with photos, which was a great way for us to still feel connected while away :)

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Fahad A.
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: Angel B.
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Angel B.
from
$50
per day
4.8 out of 5 stars
6 reviews
2 years of experience
South Shore, Chicago, IL, 60649

About: Im a genuine person, with about 5 years of pet sitting, reliable and understanding. Im proud to say I have a lot of experience with all sorts of animals. My whole family being full of pet lovers so I’ve been handling caring for animals most my entire life, from cats to ducks, turtles and dogs. I’ll be able to work with your schedule if you’re willing to work with mine. I love dogs and all pets, so your child will be in loving hands. I’m easy to reach and great with last minute scheduling. I look forward to working with you and your little one. I know a (wo)mans pet is their best friend, there’s no one better to give that responsibility to besides myself. I’d look out for you and your family member they way I’d look out for my very own. I have open availability and I can work with your schedule, for house sitting Im allowing 4 friendly dogs per stay up to 1 week, please provide valid contact information as well as all your pets basic needs, additional rates apply for any supplies I may need during their stay. As well as emergency contact thank you I have a gated apartment as well as being located next to a popular dog park, I do 3 walkies a day, morning, afternoon and night. As well as a designated space for dogs to roam in my apartment, I’m well maintenance and organized.

Sitter Profile Image: Tamyra L.
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Tamyra L.
from
$55
per day
4.7 out of 5 stars
19 reviews
4 repeat clients
15 years of experience
Grand Crossing, Chicago, IL, 60619

About: My name Is Tamyra and I have been caring for animals for over 15 plus years !! Since I was about 6 years old ! I have had all types of animals before from dogs and cats to fishes and frogs ! I absolutely love animals but I love dogs and cats the most !! I treat animals as if they were children ! They are just sweet babies with puppy eyes LITERAL puppy eyes ! I guarantee your animal will be loved and taken care of while in my care ! Your pet will go home even better then how they came to me ! That’s it for now but I can’t wait to spend time with your fur babies ! I am currently a stay at home mom so pet care fits into my daily schedule perfectly ! I will be using rover as a full time job genuinely caring for animals is the way I will make my money I have lots of toys and snacks for your fur babies ! I include daily walks and runs as well as play time ! Your pets are free to roam and lay as they please I’m currently a stay at home mom .. so I have plenty of time to interact with and play with the pup ! It also helps me to keep active ! I have a enclosed fenced in front yard as well as back yard ! I also have a husband who is very supportive and helps me out tremendously! I can also crate your pet if your pet is crate trained and knows how to be in a crate

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Adventure-ready dog walkers - Woodlawn

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: 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: 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: Manuela G.
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Manuela G.
from
$23
per walk
5.0 out of 5 stars
28 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, IL, 60637

Manuela is great with my dog, very reliable and easy to communicate with. It makes my workday less stressful to work with her and i appreciate her a lot.

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Jennifer D.
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: Danielle K.
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Danielle K.
from
$20
per walk
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: Sarah W.
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Sarah W.
from
$20
per walk
3 years of experience
Woodlawn, Chicago, IL, 60637

About: Taking care of dogs was the first job I ever had. Neighbors would have me come over after school to check in with their babies and play with them or take them on walks. I've also been lucky enough to watch people's dogs while they were out of town; including puppies! Most recently, I volunteered at an animal shelter where we would take animals for walks, train them, bathe them, and shower them with love and treats! Every dog is unique, and I enjoy taking the time to get to know each animal and their family. I am currently working part-time with a flexible schedule, so I have plenty of time to accommodate specific schedules and adapt to individual needs. I always approach caring for animals with safety and respect as a first priority. It is important to me that both the dog and I are safe, and that I am attuned to their needs. I also want to prioritize respect for other people's space and time, so I make an effort to always be on time and adapt to any individual requests in people's homes.

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: Beverly B.
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Beverly B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
273 reviews
107 repeat clients
7 years of experience
Chatham, Chicago, IL, 60620

We have been consistently using Beverly since our pup was 3 months old. Beverly does weekly walks for us as well as daycare and overnight stays. Charley loves her Beverly and she has quickly become part of our family.

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Sandy M.
Sitter Profile Image: Kristen M.
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Kristen M.
from
$20
per walk
10 years of experience
Hyde Park, Chicago, IL, 60637

About: I have experience taking care of all kinds of pets (mine and others) since I was a kid! Spent my life around all sizes of dogs, and I’m a lover of all cats! I’m a recent MA graduate, so my schedule is very open! I’m a very active person and enjoy walks, so I’m a great option to take your pup on midday walks! I have lots of experience around cats and dogs, so I will always make sure to help them feel comfortable in their space by building up trust between us!

Sitter Profile Image: Katarina S.
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Katarina S.
from
$16
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve taken care of multiple dogs of varying ages and have always enjoyed it immensely. I no longer have a dog of my own but I would love to make friends with yours. I am working 3 days per week (not a set schedule) and have enough time to spend with some lovely dogs. My schedule changes week to week but I am quite flexible and hopeful we can find a good agreement for dog sitting/walking. My apartment is clean and spacious and perfect for a small/medium dog to stay at and play. I do not own a crate but also would prefer if your dog is properly trained and can tolerate being in open space.

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: Zoe E.
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Zoe E.
from
$18
per walk
5.0 out of 5 stars
2 reviews
4 years of experience
Hyde Park, Chicago, IL, 60637

About: I love both dogs and cats. I have been fostering cats for the last four years, from kittens to senior cats, with a range of personalities. I have also provided free catsitting services to the foster organization I work with. I grew up with dogs and am very comfortable with all kinds of dogs--but I especially love big dogs! I am a responsible law student with a flexible schedule as I study for the bar exam. I am currently finishing up law school, with only one class per day, so I have a flexible schedule that can work around your preferences. I do not plan to have pets in my home because I currently have a foster cat of my own! But I am very respectful of others' spaces and will leave it just as I found it. I can let your dog out in a yard or take him or her out on a walk.

Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$25
per walk
5.0 out of 5 stars
26 reviews
5 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

Rebecca is so reliable! She walked Spot on a regular schedule for 2 months and it was a relief knowing that someone was giving my pup a great midday walk and some love while I was at work.

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Michaela J.
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: Tynetta H.
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Tynetta H.
from
$20
per walk
4.5 out of 5 stars
2 reviews
1 repeat client
5 years of experience
Chicago, IL, 60619

About: Hi there! I'm Tynetta, your neighborhood work-from-home pet auntie. 🐾 I work remotely during the day, which means your furry family member gets plenty of company, potty breaks, playtime, and belly rubs instead of being left alone for hours. Whether your pet is a professional napper, an energetic explorer, or simply wants someone nearby while they snooze, I'm happy to match their pace. Outside of pet sitting, I work in public health and spend my days helping people build healthier communities. Friends would describe me as calm, dependable, and ridiculously organized. Pets seem to appreciate that too. I'm happy to send regular photo updates (expect lots of candid "living their best life" moments), follow your pet's routine closely, and make sure they feel safe, loved, and at home while you're away. A few fun facts about me: • I work from home, so your pet gets lots of companionship throughout the day. • I'm an early riser and love getting outside for walks. • I'm patient with shy pets and enthusiastic enough for the zoomie crowd. • I'm the kind of person who will absolutely learn your dog's favorite toy, your cat's preferred napping spot, and all the little quirks that make them who they are. I know how important it is to trust the person caring for your pet. My goal is simple: when you come home, your pet is happy, relaxed, and maybe just a little disappointed that their vacation with me is over. I can't wait to meet you and your best friend! Pet care fits naturally into my routine because I work from home most days. That means I'm around to provide regular potty breaks, walks, playtime, meals, and plenty of companionship throughout the day. I genuinely enjoy having a furry coworker keeping me company while I work! I also like starting and ending my day with walks, so caring for pets blends seamlessly into my schedule without leaving them alone for long stretches. I believe pets are happiest when their routines stay as consistent as possible. Whether I'm caring for your pet in my home or yours, I'll follow their feeding schedule, exercise routine, medication instructions, and any special preferences you share. I'll keep their space clean, make sure they have fresh water, lots of affection (if they enjoy it!), and I'll send regular photo updates so you can relax knowing they're doing well. My goal is for your pet to feel safe, comfortable, and loved while you're away.

Sitter Profile Image: Dominique L.
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Dominique L.
from
$30
per walk
4.9 out of 5 stars
47 reviews
21 repeat clients
5 years of experience
Woodlawn, Chicago, IL, 60637

Mack has been loving having Dominque walk him during the week! She’s been very prompt and always lets me know when she starts and ends her walk.

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Dianna T.
Sitter Profile Image: Monique O.
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Monique O.
from
$30
per walk
5.0 out of 5 stars
4 reviews
25 years of experience
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 .

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Over 980,000
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Large dog specialists near you - Woodlawn

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: 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: 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: 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: 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: 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: 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.
Sitter Profile Image: Tamya O.
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Tamya O.
from
$43
per night
5.0 out of 5 stars
4 reviews
4 years of experience
Woodlawn, Chicago, IL, 60637

I am impressed by how seriously Tamya is taking this job. She gave me a long list of information about Ivy to complete, so that she can get to know her well before the job starts. Tamya also posts photos of Ivy often, so I can see that she is doing well. I highly recommend her.

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Lin P.
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

Ashley is very professional, gives great updates about your pup, and takes the job of caring for your pet seriously! 10/10, would strongly recommend.

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John I.
Sitter Profile Image: Mercedes M.
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Mercedes M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
63 reviews
21 repeat clients
15 years of experience
Alsip, IL, 60803

Mercedes is great with my Poo. He is fully engaged with other dogs his size & loving humans for when he taps out🤣. I’m completely at peace when I drop him off…the picture collection confirms her attentiveness & care for our dogs 🐶.

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Arlette P.
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: Kathleen K.
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Kathleen K.
Star Sitter
from
$48
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
3 years of experience
Evergreen Park, IL, 60805

Excellent! She took great care of my little boy. No hesitation I would use her again if in the area. Good communication and accommodating.

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Chuck E.
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: 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: 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: 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.
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