Dog Boarding in Woodlawn, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Doggy Day Care
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Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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1. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
245 reviews
106 repeat clients
from
$45
per night

Liz was awesome! Our puppy had an unfortunate accident the day we dropped him off by houdini-zing out of his crate and subsequently stealing ALL of his training treats off the shelf. Needless to say, he had some tummy issues that Liz was so patient in dealing with. We felt terrible but her positivity and patience with him made us feel like he was in such good hands. Liz sends pics and daily updates. We’re so thankful!

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Sitter Profile Image: Beverly B.
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Sitter Profile Image: Beverly B.
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2. Beverly B.

Home full-time, individual care
Chatham, Chicago, IL, 60620
2.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
234 reviews
85 repeat clients
from
$37
per night

Beverly was great with Rocky. He's a puppy with a lot of energy and she gives him the opportunity to run around as well as the attention she needs. She keeps me updated and is extremely flexible. Rocky enjoys his time with her and will definitely be going back.

Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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3. Ebonee A.

12 + years of Vet-Tech experience!
Hyde Park, Chicago, IL, 60615
1.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
30 reviews
14 repeat clients
from
$50
per night

Ebonee is absolutely amazing! Beautiful spirit, warm, and welcoming. My fur baby felt at home and probably has found his permanent sitter! Thanks for being an amazing 2nd home for Brownie! We’ll definitely see you again!

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Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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4. Kyle H.

Rover 101
Over a decade of experience!
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$55
per night

My dog has boarded with Kyle a few times and is always sooo happy to see her. She clearly has a way with dogs. I would recommend her and definitely use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ra'eesa S.
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Sitter Profile Image: Ra'eesa S.
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5. Ra'eesa S.

Extraordinary pet care! :)
Woodlawn, Chicago, IL, 60637
0.2 mi. away
Boarding
5.0 out of 5 stars
18 reviews
6 repeat clients
from
$45
per night

Ra'eesa was so good to our pup. I felt like she treated him as her own and I loved that! Provided videos and pictures the entire stay, which made me feel so comfortable being that its my kids and I first pup. After the stay I told Ra'eesa Snowy will be back anytime we need a sitter ? Thanks you!

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Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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6. Tania B.

Rover 101
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
5.7 mi. away
Boarding
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$50
per night

Tania is AMAZING!! Our dog is happy and healthy when we picked her up. She sent updates throughout our time away. She is very quick to respond. She is also very thorough when caring for our dog. Would highly recommend!

Sitter Profile Image: Tonisa J.
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Sitter Profile Image: Tonisa J.
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7. Tonisa J.

Rover 101
Your pups second home....
Calumet Heights, chicago, IL, 60617
3.1 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
68 reviews
31 repeat clients
from
$55
per night

Tonisa was such an amazing sitter my baby Blanca looks so happy in all the pictures. I definitely will be using her again , it truly eased my mind knowing Blanca was ok. Thank you again Tonisa we appreciate all you did with her. Monica

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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8. Viola R.

A dogs best friend
Hyde Park, Chicago, IL, 60615
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$30
per night

Viola did a fantastic job on taking care of my Zoë. She sent updates and pictures of everything that she had been doing for Zoë. I saw how comfortable she made Zoë feel being in her care. I will definitely have Viola to take care of Zoë again whenever Viola is available.

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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9. Courtney B.

Your Dog's Favorite Sitter
Grand Boulevard, CHICAGO, IL, 60653
2.6 mi. away
Boarding
5.0 out of 5 stars
17 reviews
5 repeat clients
from
$39
per night

My dog immediately gravitated towards Courtney's calm and caring demeanor which let me know my dog would do well in her care! Like any dog owner, ensuring that my dog is safe, happy, and comfortable while on vacation is a top priority. Courtney provided prompt communication, daily updates, and made sure my dog felt right at home. I would rebook again! If you are looking for quality care for your dog, do not hesitate to book with Courtney! :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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10. MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
1.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
12 reviews
1 repeat client
from
$40
per night

My dog was taken care off even though she is particular with her habits. María José always keep me updated and made me feel good and at easy while I was out of town. Thank you!

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Sitter Profile Image: Holly R.
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Sitter Profile Image: Holly R.
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11. Holly R.

Your Pet's Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
0.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
76 reviews
35 repeat clients
from
$60
per night

Holly did a great job giving our very attached dog lots of cuddles and attention during his stay with her. She shared pictures and communication, which also put us at ease. We were confident he was in great hands and will be back!

Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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12. Ashley B.

Open house for Pets
Hyde Park, Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
74 reviews
38 repeat clients
from
$75
per night

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.

Sitter Profile Image: Dwight C.
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Sitter Profile Image: Dwight C.
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13. Dwight C.

Rover 101
Work from home - large fenced yard
Woodlawn, Chicago, IL, 60637
0.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
151 reviews
65 repeat clients
from
$30
per night

Simply put, Dwight is everything you’d want in a dog sitter. He works from home, has a yard, and makes sure the dogs have a lot of activity. He is incredibly responsive and sends great photos to keep you updated. Beyond that, he’s just an awesome guy. I have a demanding schedule and he is incredibly flexible and willing to accommodate. Will use over and over again.

Sitter Profile Image: Tashea’ & Dushan M.
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Sitter Profile Image: Tashea’ & Dushan M.
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14. Tashea’ & Dushan M.

14 years of dog care and love!
Auburn Gresham, Chicago, IL, 60620
4.0 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

Tashea and Dushan did an amazing job watching my 2 month old American Bully. I was nervous because it was my first time away from her, but they kept me updated with pictures and videos and she looked super happy in every single one. I highly recommend them for dog boarding.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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15. Makeba L.

WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
2.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
13 reviews
10 repeat clients
from
$47
per night

One of the best experiences I've ever had! Makeba was wonderful and took great care of my fur baby Benny. I absolutely recommend Makeba's services!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tanisha & Darrius T.
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Sitter Profile Image: Tanisha & Darrius T.
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16. Tanisha & Darrius T.

Rover 101
🐾❤️ Comfort means everything ❤️🐾
Ashburn, CHICAGO, IL, 60652
6.5 mi. away
Boarding
5.0 out of 5 stars
120 reviews
33 repeat clients
from
$50
per night

Tanisha and Darrius did an excellent job with an overnight say with my pup. I had a last minute trip I needed to take and they were available and willing to help me out. There communication was excellent and informative. My dog who is usually stressed in rush situations and gets sick, came home happy, healthy and rested well. Items I had forgotten like his blanket were provided by them for his comfort. I received pictures of his daily activities from nap time to playing in the back yard with some new friends. My dog was not ready to come home when being picked up and that's exactly the kind of stay I was hoping he would have. I was at ease of his well being during my trip and will be utilizing Tanisha and Darrius many more times in the future.

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Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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17. Ashley M.

Rover 101
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
6.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
44 reviews
19 repeat clients
from
$52
per night

Ashley was a wonderful host for Beck. She was super responsive, friendly, and professional. She kept us updated throughout his stay and provided pics as well. We felt very comfortable leaving Beck in her care. Will definitely plan to book again.

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Sitter Profile Image: Nakeisha B.
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Sitter Profile Image: Nakeisha B.
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18. Nakeisha B.

Rover 101
Your fur baby will be in good hands
Grand Crossing, Chicago, IL, 60619
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
63 reviews
24 repeat clients
from
$55
per night

Nakeisha was wonderful! She was very communicative throughout the entire process. She gave me frequent updates about my cat with pictures and videos.

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Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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19. Andrew T.

WFH Couple, Park Nearby
Lower West Side, Chicago, IL, 60608
6.9 mi. away
Boarding
5.0 out of 5 stars
102 reviews
42 repeat clients
from
$45
per night

Such a great experience with Andrew and his lovely wife. My Poppy was well taken care of, and I received lots of picture updates. Andrew is very communicative and easy to work with. So great that I’m bringing her back tomorrow! Thank you!!!

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Sitter Profile Image: Mia S.
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Sitter Profile Image: Mia S.
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20. Mia S.

Dog lover! WFH/Fenced backyard
Roseland, Chicago, IL, 60628
5.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$38
per night

Hire her!!!!!!! Mia took amazing care of Wally while we were away on a weeklong vacation. He can get pretty anxious and homesick, but he settled in with Mia right away. He was eating his meals and playing with her adorable dog Bentley in no time. We miss him dearly when we’re away and she sent tons of photos and videos so we could see what a good time he was having. The backyard was great fun for him. 10/10 would recommend working with Mia ❤️

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Rover also offers Dog Boarding in these neighborhoods:

Rover also offers other services in Woodlawn:

Dog lovers in Woodlawn, Chicago, IL love dog sitters on Rover.com. Over 7915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Woodlawn dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Woodlawn, Chicago, IL, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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