Dog Boarding in Woodlawn, Chicago

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

1. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

8 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)"

2. Amanda

I'm a student and I love dogs!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

"Amanda was awesome taking care Willow. Willow felt at home and her had routine walks outside. And picture updates were much appreciated. Would definitely ... (more)"

3. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

4 repeat clients

"Great job and kept me up to date with pictures. She deserves a great, but of course it would be more self serving not to, since people will find what I've fo... (more)"

4. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

37 repeat clients

"Kristal was awesome. Very friendly and accommodating. Went above and beyond to make my dog feel comfortable. I highly recommend her. Wonderful spirit. Thanks... (more)"

5. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"I cannot express enough how wonderful Ebonee is! Our fur baby stayed with her for two weeks while we were on vacation. She keep us updated with pictures and ... (more)"

6. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

7 repeat clients

"Saran was a wonderful sitter for my bichon frise. She was warm, friendly and sent lots of updates and pictures. This was my first time using Rover and, as ... (more)"

7. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

8 repeat clients

"Marga and her roommate have taken amazing care of our dog when we've had to leave town. Both times, they've taken him not just on walks but on outdoor advent... (more)"

8. 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)"

9. Anquin

Young Dog Friendly Professional

Hyde Park, Chicago, IL, 60637

Dog Boarding

1 repeat client

"Bella enjoyed her stay and really liked playing with Aria. (more)"

10. 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 very accommodating with drop off and pick up times with the dogs. She took great care of our two elderly dogs and made them feel as at home as h... (more)"

11. Shamika

Hello to all my pet parents

West Englewood, Chicago, IL, 60636

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

About: Hi i am a 30yr old pet lover i have always loved animals since i was a child, not to good with bugs, but cats, dogs, snakes, little furry things yo... (more)

12. 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)"

13. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"Blaize did a fantastic job with our pups. She watched them for a whole week, and did everything she could to put us and our dogs at ease during that time. We... (more)"

14. Emily

I'll run with your dog!

Hyde Park, Chicago, IL, 60615

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

"Emily did a great job with Clover! She sent some very cute pictures which is a definite plus. (more)"

15. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"My dogs love and adore LeAnna! As soon as they see her, they jump, slobber and stick to her like glue. She babysat my pups for a week, I totally trusted he... (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. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

10 repeat clients

"Lynettra is the best dog sitter we've ever hired. She is professional and easy to work with. Our dog has stayed with her twice, once for a month and another ... (more)"

18. Laura

Teacher by day... Dog lover by life

Kenwood, Chicago, IL, 60615

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

1 repeat client

"Laura was great with my dog Bella! She really enjoyed her stay with long walks to the lake and playing non stop with Laura's sweet dog Spaghetti. Definitely ... (more)"

19. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"Kyle and Kimberlie were fantastic. They boarded our dog for 2 weeks over the summer and we received frequent email updates with lots of pictures. When we m... (more)"

20. Anna

I'll cuddle & exercise your dog!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Anna is the most friendly dog loving human I have met in my entire life. She would drop anything to help her own dogs as well as anyone else's. She is an inc... (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: