Dog Boarding in Woodlawn, Chicago

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

1. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

3 repeat clients

"Gail was so great with my dog, Oliver. I have a pretty clingy shih tzu and after trying two sitters for him, I thought we just couldn't leave him alone anymo... (more)"

2. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney was an AMAZING dog sitter! She was very flexible and accommodating with her schedule and she stayed in constant contact with me keeping me up to dat... (more)"

3. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"Tatiana was great with my dog Lucy. She was accommodating to our travel situation, concerned when Lucy was not eating because of some anxiety she experienced... (more)"

4. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

6 repeat clients

"Great stay for Tio. He had plenty of walks and fun with doggie day care visitors. Nice location near a park. Back yard available for scratching his back wi... (more)"

5. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 repeat clients

"Marga did such a wonderful job with our pup! We were out of town for almost 5 days and she attentively cared for our dog and sent regular updates. Our dog, L... (more)"

6. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

"Breana will be the perfect fit as your dog sitter. She is responsible, hardworking, and organized. Breana has grown up with dogs and she certainly knows what... (more)"

7. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

34 repeat clients

"Kristal and her family were great. Our dog, Lola, had a great time. She warmed up to Kristal's dogs and loved playing with them in the family's yard. She ... (more)"

8. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"Kimberly was so great with my dogs!!!! She sent updates and pictures showing they were obviously comfortable and happy throughout their stay and was very acc... (more)"

9. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

10. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

"Lynettra was very kind and my dog Butters was happy with her! :) (more)"

11. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Drop-In Visits

About: Hello and welcome to my profile. I'm Saran, a professional and passionate dog lover. I love that dogs love us unconditionally, they're giving and ... (more)

12. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Our dog only spent 24 hours with Martineja, but it was clear that she enjoyed having our dog there. Everything seemed good and fine, and our dog was happy. ... (more)"

13. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was amazing!!! By the looks of the pictures, our dog enjoyed his stay! She sent updates about twice a day which was great! I was glad I left him in the... (more)"

14. Aaliyah

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

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

"Aaliyah was excellent. extremely flexible and willing to work with you. Highly recommended (more)"

15. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"LeAnna is passionate about animals and loves pups of all shapes and sizes. She routinely stops and asks dog owners if she can pet their dogs, always engagin... (more)"

16. Brandy

Exp. & Resp. Ph.D. animal lover!

Hyde Park, Chicago, IL, 60637

Dog Boarding

"Brandy took great care of our dog, Noodles. We had arranged a pre-stay meeting to ensure everyone would get along, and then a few weeks later we dropped Nood... (more)"

17. Dana

Hyde Park Animal Sitter for Hire!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

2 repeat clients

"Dana was extremely nice, kind & professional. I would take Macky back to Dana any time. (more)"

18. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ÔŁĄTHEM

Grand Crossing, Chicago, IL, 60619

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

About: Hi , My name is Keeshina As a kid Me & my sisters Loves any pet we come in contact with!! My sis has 2 pits 2 cats ...my other a Lil tea cup! I ha... (more)

19. Shellie

Love dogs, owned them for years

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care

"After receiving the bad news that I could not board my dog Rocket with any of the major boarding facilities in the Chicago surrounding area I conducted a sea... (more)"

20. MICHAIAH

Ready for Your Rover!

Chatham, CHICAGO, IL, 60619

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

About: I love animals and they love me. I'm very loving and my space is pet friendly! Pit bulls are my favorite and I enjoy the company. I always wanted m... (more)

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Learn About Premier

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: