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

kamiah and cassius were wonderful and i highly recommend them. they took great care of my dog. quick communicators, very professional, and they were kind when i was running late. i am looking forward to booking with them again!

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David B.
Sitter Profile Image: Brandon E.
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Brandon E.
from
$42
per night
5.0 out of 5 stars
22 reviews
12 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

"Brandon is an excellent and reliable dog sitter. He provided exceptional care for my dog, Cookie, ensuring she was happy and well-tended to. I highly recommend his services for anyone looking for dependable pet care!"

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Donnie S.
Sitter Profile Image: Bola A.
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Bola A.
from
$54
per night
4.9 out of 5 stars
172 reviews
64 repeat clients
15 years of experience
Woodlawn, 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: Tonisa J.
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Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
80 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

Tonisa was great, she was always responsive and kept us up to date with pics throughout our trip. Deuce seemed to have a great time at her house. Thank you Tonisa!

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Andre W.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
377 reviews
178 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Teddy is our 150lb Bullmastiff and EK and her family welcomed him like the rest of the tiny tots that are looked after daily. She is trustworthy and reliable. We hadn't been on a real vacation in 2yrs we had no issues or worries while gone.

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Susan L.
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 was wonderful: responsive to questions, available for convenient drop off and pick up, and truly someone who cares for animals. Would recommend him hands-down!

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

Dominique was AB-SO-LUTE-LY Fabulous!!! She treated my babies like her very own (even calling them by their "cutesy" baby names when she scratched them under their cheeks and behind the ears). She created a safe, loving and clean space for them... allowing them to thrive. Truth be told, I'm kind of jealous that they "took to her" so quickly and didn't miss me more (our first time separated in 11 years). Knowing Dominique was taking such great care of them, made the stressful time I was going through easier to manage. My babies came back, calm,well feldand clean!!! 👍 I will definitely seek out Ms. Dominique again for any and all future pet needs.

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Melody K.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
25 reviews
11 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: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
250 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Very kind and professional. I would pick her again when I need another sitter for my bunny. First time ever doing this and she gave me the best experience

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

Shani (and her kiddos☺️) LOVED on my pup while I was away. Shani was an excellent communicator and sent update photos and videos, too. I really appreciated such good communication and how well Lady was taken care of. When you see your dog smiling in the update photos, you know it’s real. I’ll be looking to book Shani for my next trip away.

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

Ania is amazing! She’s checked in with pix and videos daily. My pup came home so happy and content. I’ll definitely be checking her schedule the next time I need a sitter. 10/10 ☺️

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Davinelle 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: Dajah P.
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Dajah P.
from
$35
per night
5.0 out of 5 stars
3 reviews
4 repeat clients
1 year of experience
Englewood, Chicago, IL, 60605

Thank you Dajah for taking excellent care of Milo for these past five days. We're looking forward to the next time!

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Harold D.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
190 reviews
68 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Really appreciate Ashley take care of our dog for a long weekend! Ashley is super considerate and communicative - you can expect to receive regular updates on how your pup is doing and you can tell she goes to great lengths to ensure every pet that stays with her has a great experience. I would absolutely choose Ashley again for boarding!

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Rosalie C.
Sitter Profile Image: Tanisha & Darrius T.
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Tanisha & Darrius T.
Star Sitter
from
$52
per night
5.0 out of 5 stars
149 reviews
39 repeat clients
16 years of experience
Ashburn, CHICAGO, IL, 60652

Tanisha was AMAZING. Her commutication was awesome and my dog loved her visit. Tanisha helped My dog with her socializing skills and made sure to send me plenty of pictures and videos. I highly recommended Tanisha and will be back!

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Lauren W.
Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$55
per night
5.0 out of 5 stars
191 reviews
48 repeat clients
11 years of experience
Near South Side, Chicago, IL, 60605

The BEST sitter we could’ve asked for! So attentive, with such a great attitude, constant communication and sweet updates throughout the day. Made us feel so calm about our little Yorkie staying with Katrina. Wonderful experience all around, would definitely be coming back! Thank you for taking such a great care if my baby :)

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Ksenia S.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
39 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: Cassandra B.
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Cassandra B.
from
$40
per night
5.0 out of 5 stars
9 reviews
2 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: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
19 reviews
16 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

We have a 14 year old dog who’s regular sitter could not commit to our 3 week Australia trip so I was nervous to find someone new for an older dog. Cheyanne is amazing, she has experience with older dogs and special needs, my dog was so happy with her and even found a “boyfriend” during her long stay. I did not hesitate to book her again for another long trip, our baby ran out of food but Cheyanne went to the store to buy her more “fresh pet” and even gave her a bath! Our dog loves being a high rise dog and Cheyanne spoils her just like we do.

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Gina M.
Sitter Profile Image: Manuel P.
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Manuel P.
from
$38
per night
4.9 out of 5 stars
47 reviews
15 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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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
55 reviews
17 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60637

rachel was AMAZING! she made me feel completely at ease when i was so anxious about leaving my babies alone. she was so thorough and loving and really cared for them as they were her own. her constant checkins and photos were so reassuring and felt like i could see my babies everyday even if i was far away! i would book her EVERYTIMEEE!!!! book her you wont regret it! im so happy i can vacation now with ease knowing i have rachel!!

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sana h.
Sitter Profile Image: Coretta S.
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Coretta S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
280 reviews
102 repeat clients
3 years of experience
South Shore, Chicago, IL, 60649

Coretta is great! Appreciated the care she showed my cats, as well as her updates while I was traveling. Felt so much better leaving the country knowing they were being cared for so well.

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Tiffany G.
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: Maya C.
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Maya C.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
112 reviews
44 repeat clients
8 years of experience
Chicago, IL, 60615

Maya is an excellent cat sitter with tons of experience. she's kind and patient and professional and worked really well with my cat who is a little anti-social and easily spooked. i would highly recommend maya to anyone

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Stephen Y.
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
15 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: Qutress T.
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Qutress T.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
84 reviews
33 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q has quickly become our go-to pet sitter. She always provides top-notch care, and we love that she is often accompanied by her son, who our cat absolutely adores.

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Connor R.
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.
Sitter Profile Image: Manuela G.
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Manuela G.
from
$11
per visit
5.0 out of 5 stars
26 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: Zoe E.
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Zoe E.
from
$14
per visit
4 years of experience
Hyde Park, Chicago, IL, 60637

About: I have fostered cats from 2 months old to adults, with a range of personalities, including affectionate, calm, playful, hyper, or independent. I like to get to know each cat's unique traits to provide the best care for them. I am happy to engage your cat in active play, to socialize them, or to give them space. I can accomodate a range of medical or dietary needs.

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 took care of our two cats while we were away. Everything went fine! Thanks Jessy.

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Marie S.
Sitter Profile Image: Mia L.
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Mia L.
from
$18
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
3 years of experience
Hyde Park, Chicago, IL, 60615

Mia was incredible with my cat Stormie! We were able to quickly schedule a meet and greet for her to meet Stormie and I could already tell she genuinely cared. She asked questions about feeding, whether Stormie likes to sleep in the bed, daily routine, and took notes when I explained some food changes due to Stormie's sensitive stomach. It is VERY clear she does truly love and care for animals. We had Mia watch Stormie for the weekend and came back to the apartment being clean, litterboxes were empty and freshly cleaned, etc. Mia sent regular updates as well with photos and videos of Stormie so I knew that everything was going smoothly. She also sent messages regularly about how they were playing with toys, how Stormie was doing, etc. I 100% will book with Mia again as I truly never felt more comfortable with someone watching my baby before now.

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Lillian W.
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

An amazing cat sitter! It’s clear how much she truly loves animals, and they love her back. Even our very shy and unsociable kitty fell in love with her at first sight, which was a huge surprise to us. We’re so grateful for her care, kindness, and attention.

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Anastasiia 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

Rachel was a wonderful cat sitter for our two cats during the holidays! She is very responsive, kind, and even earned the trust of our very shy cat. She took great care of them and I would definitely book with her again.

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Ivy Y.
Sitter Profile Image: Ava M.
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Ava M.
from
$18
per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
7 years of experience
Hyde Park, Chicago, IL, 60637

Ava went above and beyond watching my 3-year old golden. She clearly loves dogs and loves her job. Would be happy to book with again.

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Jada D.
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

Becca took exceptionally good care of our cat Autumn while my housemate and I were abroad. It had been hard to find good, reliable care (esp. due to some last minute travel plan changes on our part) but Becca stepped right in and everything went smoothly! Becca checked in everyday with updates and info and made sure to ask for tips to help Autumn adjust to having a relative stranger in the house. Thank you again for taking such good care of Autumn and giving is peace of mind while we were away!

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Danielle W.
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: Amiyah W.
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Amiyah W.
from
$14
per visit
3 repeat clients
1 year of experience
Grand Boulevard, Chicago, IL, 60615

About: I've taken care of multiple cats. I even have cats of my own so I am familiar of what they like and how to care for them. I have previous experios with caring for cats who have medical needs.

Sitter Profile Image: Bella B.
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Bella B.
from
$20
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
4 years of experience
Chicago, IL, 60615

Bella is so sweet and we came back to a very happy cat. Would book with her again!

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Joanna A.
Sitter Profile Image: Ashleigh P.
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Ashleigh P.
from
$18
per visit
5.0 out of 5 stars
52 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 - 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
172 reviews
64 repeat clients
15 years of experience
Woodlawn, 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: Brandon E.
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Brandon E.
from
$50
per day
5.0 out of 5 stars
22 reviews
12 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

About: Dawggy Pawties is a premium doggie daycare and enrichment retreat located in a peaceful rural setting designed specifically for city dog owners who want their dogs to experience freedom, exercise, fresh air, socialization, and structured care in a safe environment. The business includes pickup and drop-off transportation, outdoor play, socialization groups, nature walks, enrichment activities, and optional overnight boarding This is my full time job, so your pups will have my undivided attention!! My mornings start as early as 530 and end as late as 11 Your pooch will be with my family and I in our home as well as on our Farm that includes a private Dawg Pawk we also will visit different dog parks around the city of Chicago and trips to beach and other dog friendly places to provide proper socialization and public manners. your dawg will be provided with his/her own private crate to chill and relax during their stay!

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
57 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: E K.
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E K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
377 reviews
178 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Elizabeth was a pleasure to deal with from first contact until we picked Tika up at the end of the night. Amazing communication and pictures.

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David B.
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: Tamya O.
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Tamya O.
from
$35
per day
4 years of experience
Woodlawn, Chicago, IL, 60637

About: I have hands-on experience caring for dogs of all sizes, breeds, and energy levels, including active and strong working breeds. I focus on creating a safe, structured, and stress-free environment while making sure every dog gets the attention, exercise, and care they need. I’m comfortable with walks, feeding schedules, crate routines, basic obedience reinforcement, and handling energetic dogs with patience and consistency. Pet parents can expect dependable communication, regular updates, and someone who genuinely treats their dogs like family. Your dog’s safety, comfort, and routine come first. A typical day includes structured walks, playtime, exercise, water breaks, feeding according to your instructions, and plenty of attention. I keep a calm and clean environment while making sure each dog gets the right balance of activity and rest based on their personality and needs. I’m especially comfortable with active and strong breeds, so dogs that need confidence, structure, and engagement are in good hands. Whether your pet needs a relaxed companion, exercise, or consistent care while you’re away, I aim to make the experience stress-free for both you and your dog. You’ll receive updates, photos, and quick responses throughout the stay so you always know how your dog is doing.

Sitter Profile Image: Dominique F.
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Dominique F.
from
$40
per day
4.6 out of 5 stars
71 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: 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: Danielle K.
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Danielle K.
from
$35
per day
5.0 out of 5 stars
8 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: 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

My dog hates being away from me, but Dwight has been really understanding of his needs and my dog is already warming up to him after a few visits! It's great to have someone as kind and as great with dogs in the neighborhood!

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Sanja M.
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: Pratik J.
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Pratik J.
from
$35
per day
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I've been with pets all throughout my life. I've taken care of dogs, cats, rabbits, tortoises, parrots and fishes. I have a labrador Casper and a golden retriever, Remmy back home in Nepal, whom I miss every day. So I'm just looking for ways to spend more time with pets here. I work remotely as a software engineer, so my work schedule is flexible. I have lots of free time during the day, so I'm looking to walk dogs. In the past, I've walked dogs to the lake which is just 30 mins walk from home and I just chill at the lake with the dogs I'm taking care of, and also get some minor work done on my laptop. I live in a two bedroom apartment, so there's enough space for a pet. I usually walk dogs to the lake, which is just 30 mins walk from my place.

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: Alexis W.
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Alexis W.
from
$80
per day
5.0 out of 5 stars
27 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: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
4.9 out of 5 stars
250 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
39 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: 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: Eleni V.
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Eleni V.
from
$33
per day
15 years of experience
South Shore, Chicago, IL, 60649

About: I have always cared for the cats of my neighbors in Chicago, let alone other cats. Since my young adult years, I always have had cats and have been learning how to care for them from personal experience, reading online, and visiting vets as well as volunteering at shelters in Chicago over the years or supporting fundraisers! I am available nowadays to care for your pet at my home for a short period of time. Or I could visit your home! I am aware of territory adjustments and super careful about health issues. I have experience working with children and understand how important it is to supervise and engage with pets all the time! Also, it is important to pay attention to them in terms of health and behavior and provide a healthy routine of meals and clean litter boxes, among other things.

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: 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.

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

Manuela did a great job! My dog Ella really enjoyed walking with her. Manuela is punctual, reliable. My dog doesn't trust people easily but with Manuela, it was easy. Amazing! Thank you so much. ?

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Sue K.
Sitter Profile Image: Zoe E.
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Zoe E.
from
$18
per walk
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: Bola A.
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Bola A.
from
$30
per walk
4.9 out of 5 stars
172 reviews
64 repeat clients
15 years of experience
Woodlawn, Chicago, IL, 60637

Mother-in-law said Stella LOVED Bola and was so excited for all her walks!! The only thing she would change to make this a 5 start rating was the inconsistancy of arrival time and lack of communication in regards to being late. Overall, amazing service!! We look forward to working with Bola again in the near future!!

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Bridgette J.
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

Excellent dog walker. She is dependable, trustworthy, and amazing with my dog. I felt completely comfortable leaving my pet in her care during my vacation. She responds is a great timely manner

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Lashemia B.
Sitter Profile Image: Julia G.
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Julia G.
from
$14
per walk
5.0 out of 5 stars
4 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: Bella B.
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Bella B.
from
$25
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60637

About: In addition to taking care of my own three dogs, I have spent the past four summers working at a doggy daycare/ kennel. I have professional training and experience in taking care of animals of a variety of sizes and various needs. With over 50 dogs in our care every day, I am experienced in creating an environment that is safe, clean, and fun. I feel prepared to handle anything that is thrown my way !! I am a graduate student here in Chicago, so I have classes four days a week, but I can do walks and drop in visits for most of the afternoon, and dogsitting and walks Saturday-Monday. I am unable to take pets into my own home, but in a clients home I am prepared to work with whatever is available, including spending as much time outside as necessary and bringing treats and a slip lead to help with walking, training, and crating. For pets who prefer to spend their time indoors, I will make sure they still get plenty of attention and mental stimulation.

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: Ashleigh P.
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Ashleigh P.
from
$19
per walk
5.0 out of 5 stars
52 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: Danielle K.
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Danielle K.
from
$20
per walk
5.0 out of 5 stars
8 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: 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: 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: 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: Ra'eesa S.
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Ra'eesa S.
from
$25
per walk
5.0 out of 5 stars
24 reviews
8 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

About: I've cared for dogs and other pets since I was a kid. I've had the opportunity to love dogs, hampters, birds, and cats! I am and have always been reliable, trustworthy, patient, and flexible. Currently, my 6-year-old daughter and I are deciding what type of pet would be best for us, so as we decide, we thought pet sitting through Rover would be awesome! We are both very attentive and fun! Any and all instructions you leave for me will be folllowed with the upmost care to keep your pet happy! I currently work from home and part-time , so I'll have plenty of time to keep your pups happy! I'm available for boarding on both weekdays and weekends to care for pets! I have a very spacious home that your pets can run through and enjoy. I also live very close to a dog park, the lake, and many parks and open grassy areas. I will take your pet on many walks throughout the day/evening and feed them according to their schedule. They will have lots of play time and exercise!

Sitter Profile Image: Amiyah W.
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Amiyah W.
from
$10
per walk
3 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 . I am currently in school. So I will be working part time for Rover. Evening and nights works best for the weekdays and for the weekends I am open for anytime you need. For cats do have multiple cat bags if they need to brought to a appointment or any where else. And foot dogs if you don't have a leach I can get one but I would prefer for you to have leeches and rates of pets need to be taken out of the house .

Sitter Profile Image: Pratik J.
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Pratik J.
from
$25
per walk
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I've been with pets all throughout my life. I've taken care of dogs, cats, rabbits, tortoises, parrots and fishes. I have a labrador Casper and a golden retriever, Remmy back home in Nepal, whom I miss every day. So I'm just looking for ways to spend more time with pets here. I work remotely as a software engineer, so my work schedule is flexible. I have lots of free time during the day, so I'm looking to walk dogs. In the past, I've walked dogs to the lake which is just 30 mins walk from home and I just chill at the lake with the dogs I'm taking care of, and also get some minor work done on my laptop. I live in a two bedroom apartment, so there's enough space for a pet. I usually walk dogs to the lake, which is just 30 mins walk from my place.

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: Leila R.
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Leila R.
from
$20
per walk
13 years of experience
Chicago, IL, 60615

About: I have grown up with many dogs. My childhood dog grew up with me and I learned to love and take care of a dog with her. Since then I have cared for many other dogs. Most dogs I have cared for have medical needs such as medication or certain foods. While I have a soft spot in my heart (and much experience) with senior dogs, everyone loves a puppy too! I have taken care of many high energy puppies who need to play! I am available most time! I work on call so my schedule remains fairly open! I am an early riser and love a morning pet session! With my pets in my homes, I ensure they are provided evweything they need and more. Safety health and well-being are top priorities for all animals in my life. I want to ensure there is nothing toxic for your furry friend to get into, while also providing engaging activities for them!

Sitter Profile Image: Brooke B.
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Brooke B.
from
$18
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I am an animal lover and looking for ways to spoil other fur babies! I took care of my childhood dog up until I left for college, which included walking her, feeding her, entertaining her, baths, vet appointments, etc. I can adapt to the temperament of your pet and ensure that they are safe and have all of their needs met. I also love long walks and being active, so I don’t mind helping the more active pups get their energy out! I’m currently a grad student, so I have some free time to take care of your pet needs! I have class usually in the mornings, so I can run over for mid-day walks or feedings and would love to stay with your pets overnight. When I come to your home for walks/feedings or an overnight stay, I like to know as much as possible so that your pet will feel as comfortable as possible, almost as if nothing has changed. I recognize that I am in someone else’s home and respect and abide by all the rules laid out my the pet owners.

Sitter Profile Image: Ava M.
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Ava M.
from
$18
per walk
5.0 out of 5 stars
8 reviews
4 repeat clients
11 years of experience
Hyde Park, Chicago, IL, 60637

Ava was great with my dog right from the start. She is very responsive and a good communicator, she is always on time. I highly recommend her!

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Sarah L.
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!

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Over 980,000
dogs traded couch time for play time with Doggy Day Care on Rover1

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: Brandon E.
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Brandon E.
from
$42
per night
5.0 out of 5 stars
22 reviews
12 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

"Brandon is an excellent and reliable dog sitter. He provided exceptional care for my dog, Cookie, ensuring she was happy and well-tended to. I highly recommend his services for anyone looking for dependable pet care!"

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Donnie S.
Sitter Profile Image: Bola A.
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Bola A.
from
$54
per night
4.9 out of 5 stars
172 reviews
64 repeat clients
15 years of experience
Woodlawn, 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: Tonisa J.
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Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
80 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

Tonisa was great, she was always responsive and kept us up to date with pics throughout our trip. Deuce seemed to have a great time at her house. Thank you Tonisa!

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Andre W.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
377 reviews
178 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Teddy is our 150lb Bullmastiff and EK and her family welcomed him like the rest of the tiny tots that are looked after daily. She is trustworthy and reliable. We hadn't been on a real vacation in 2yrs we had no issues or worries while gone.

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

Dominique was AB-SO-LUTE-LY Fabulous!!! She treated my babies like her very own (even calling them by their "cutesy" baby names when she scratched them under their cheeks and behind the ears). She created a safe, loving and clean space for them... allowing them to thrive. Truth be told, I'm kind of jealous that they "took to her" so quickly and didn't miss me more (our first time separated in 11 years). Knowing Dominique was taking such great care of them, made the stressful time I was going through easier to manage. My babies came back, calm,well feldand clean!!! 👍 I will definitely seek out Ms. Dominique again for any and all future pet needs.

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

Very kind and professional. I would pick her again when I need another sitter for my bunny. First time ever doing this and she gave me the best experience

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

Shani (and her kiddos☺️) LOVED on my pup while I was away. Shani was an excellent communicator and sent update photos and videos, too. I really appreciated such good communication and how well Lady was taken care of. When you see your dog smiling in the update photos, you know it’s real. I’ll be looking to book Shani for my next trip away.

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

Ania is amazing! She’s checked in with pix and videos daily. My pup came home so happy and content. I’ll definitely be checking her schedule the next time I need a sitter. 10/10 ☺️

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Davinelle D.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
190 reviews
68 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Really appreciate Ashley take care of our dog for a long weekend! Ashley is super considerate and communicative - you can expect to receive regular updates on how your pup is doing and you can tell she goes to great lengths to ensure every pet that stays with her has a great experience. I would absolutely choose Ashley again for boarding!

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Rosalie C.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
39 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: Manuel P.
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Manuel P.
from
$38
per night
4.9 out of 5 stars
47 reviews
15 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: Megan S.
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Megan S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Evergreen Park, IL, 60805

Megan was so sweet!. This was the first time we needed to board our baby for a few days. Megan eased our worries. She was in contact with us throughout the day. She sent lots of pics of our baby. Definitely will be a return customer!

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Tammy T.
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

Timothy was a wonderful sitter ! He shared updates and photos regularly and gave my dog extra food because I didn’t pack enough. He was also very gracious to let me extend my booking on short notice due to travel delays. Highly recommend Timothy and hope we can book with him again !

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Michelle C.
Sitter Profile Image: Mercedes M.
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Mercedes M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
61 reviews
20 repeat clients
15 years of experience
Alsip, IL, 60803

Mercedes is absolutely amazing! She and her family treat my little fur baby like he’s one of their own, and it truly shows. He gets so excited every time he sees them, which gives me complete peace of mind knowing he is loved, safe, and happy while in their care.

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

Katie watched my dog for his first overnight stay at someone else’s house. She was absolutely amazing! She kept me up to date multiple times a day and kept my pup busy. We will definitely be booking with Katie again. Highly recommend!

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Katie P.
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

Victoria watched my Charlie while I took my trip. She always keep me aware of how Charlie is doing with plenty pictures. She has watched Charlie before and I love how she takes care of him!

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Thirisia 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: Tamya O.
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Tamya O.
from
$40
per night
4 years of experience
Woodlawn, Chicago, IL, 60637

About: I have hands-on experience caring for dogs of all sizes, breeds, and energy levels, including active and strong working breeds. I focus on creating a safe, structured, and stress-free environment while making sure every dog gets the attention, exercise, and care they need. I’m comfortable with walks, feeding schedules, crate routines, basic obedience reinforcement, and handling energetic dogs with patience and consistency. Pet parents can expect dependable communication, regular updates, and someone who genuinely treats their dogs like family. Your dog’s safety, comfort, and routine come first. A typical day includes structured walks, playtime, exercise, water breaks, feeding according to your instructions, and plenty of attention. I keep a calm and clean environment while making sure each dog gets the right balance of activity and rest based on their personality and needs. I’m especially comfortable with active and strong breeds, so dogs that need confidence, structure, and engagement are in good hands. Whether your pet needs a relaxed companion, exercise, or consistent care while you’re away, I aim to make the experience stress-free for both you and your dog. You’ll receive updates, photos, and quick responses throughout the stay so you always know how your dog is doing.

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

Nathan was great. He took good care of Tange, very responsive on the communication and even offered pick up and drop off that was very convenient.

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

Jenna was so kind and responsive! I could clearly tell in my pup’s behavior that he felt safe and comfortable with her which was a huge win for us as he often anxious! I would highly recommend her to anyone!

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Alexandria L.
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