Dog Boarding in Woodlawn, Chicago

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

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1. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

38 repeat clients

"Kristal is right up there with Mother Theresa and Ghandi in my book. I am SO thankful we found her! What a gem! She picks up AND drops-off both of our pup... (more)"

2. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Craig was great! He really cared to make Princess stay nice. He sent a picture while we were away. Princess was so happy when we picked her up. She really en... (more)"

3. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

11 repeat clients

"Marga was excellent! She took great care of TJ, was quick to respond to messages, and sent me plenty of updates during his stay. TJ isn’t the friendliest dog... (more)"

4. Dakota

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

31 repeat clients

"Dakota and Jen were very attentive to Biscuit’s needs and made his acclimation to their home very comfortable. They checked in daily to let us know how thin... (more)"

5. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

10 repeat clients

"Bob took great care of our dog while we were out of town! He gave her a lot of exercise, sent us nice updates, and was very responsive and easy to coordinate... (more)"

6. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

11 repeat clients

"Rafiki really enjoyed his stay! This was my first time leaving him with someone so I didn't know how he would respond. The daily photos and video I received ... (more)"

7. Stacey

I Love Animals and Animals Love Me

Douglas, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Every pet I've ever had Stacey took care of for me. I would honestly get jealous because my pets loved her more then me. She would tell what they wanted. She... (more)"

8. Sofia

large fenced yard to play with dog

Douglas, Chicago, IL, 60653

Dog Boarding, Dog Walking

1 repeat client

"Sofia was very sweet and flexible. She sent pics of Bok Choy throughout his stay with her, which was much appreciated (more)"

9. Susan

I love to run + chill with dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

2 repeat clients

"Susan is very sweet and accommodating. My older Staffordshire, Maximus, was well taken care of. I recommend Dudan and will definitely use her services again. (more)"

10. Amanda

Uchicago student who loves dogs!

Hyde Park, Chicago, IL, 60637

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

3 repeat clients

"Amanda was a joy to have keep our pup. He takes a moment to warm up but Amanda was able to build trust with him and before you knew it...she was giving him ... (more)"

11. Dena

Doggy Spoiler Alert

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits

18 repeat clients

"I reached out to Dena a week before a scheduled vacation due to a sudden cancellation with my usual boarder. Upon meeting I felt very comfortable with he... (more)"

12. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

15 repeat clients

"Lynettra was excellent. She came over for a meet and greet along with the other dogs that my Jill would be in her home with. She sent regular updates. She wa... (more)"

13. Khat

Pup Nation

South Shore, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

5 repeat clients

"My dog didn't get along with the original sitter's cats while I was out of town.. Khat quickly responded and even went out of her way to pick him up from her... (more)"

14. Jennifer

I will love your dog as my own.

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

"I was nervous leaving Lilly with someone I did not know instead of boarding her. When Lilly and I met Jennifer, she was so sweet, kind, and loving towards Li... (more)"

15. Aaliyah

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Aaliyah was an excellent sitter. She was very flexible with the drop off and pick up times. My pups and hers got along pretty well, which left me at ease wit... (more)"

16. Krystal

Krystal Loves the Pups

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

1 repeat client

"Working with Krystal was an excellent experience. She took great care of our dog and was easy to communicate with before and during the stay. Would definitel... (more)"

17. Henry

Fun, active, friendly grad student!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Henry was GREAT!!! Super easy to schedule/set up and very responsive. He took great care of my senior dog. Loved the photos of fetch and nap time. Highly rec... (more)"

18. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"I was thoroughly please with Ebonee' s skills as a dog sitter, because she went beyond my expectations. Having her as my pet's sitter allowed me to enjoy m... (more)"

19. Sean

"A dog's best friend"

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Sean is the best. He was very flexible and accommodating. He was superb at handling our high energy dog. I felt totally comfortable leaving him with Sean for... (more)"

20. Alison

Your dog needs a walking partner

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

"Alison was great! Super easy to work with and was so good with my senior dog! (more)"

Dog lovers in Woodlawn, Chicago, IL love dog sitters on Rover.com. Over 7,915 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.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Woodlawn, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including: