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. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

6 repeat clients

"Bob went above and beyond to make sure that our dog was comfortable and happy. He spent a lot of time with her, taking her on more walks than we asked and ev... (more)"

2. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

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)"

3. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

1 repeat client

"Ebonee was very friendly and accommodated me on very short notice. I highly recommend acquiring her services. She updated me with photos and my dog was very ... (more)"

Available this weekend
4. Samantha

Your dogs STAYcation spot!

Gage Park, Chicago , IL, 60632

Dog Boarding, House Sitting

5 repeat clients

"Samantha was amazing with my apricot toy poodle, Cinna. Since I was going to be out of town for a couple of weeks and a friend was going to dog sit my fur-b... (more)"

5. 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)"

6. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

7 repeat clients

"Saran was the BEST dog sitter ever! My Cooper fit right in with the other dogs in her home and she made sure he was comfortable! I was updated with pictures ... (more)"

7. Gabrielle

Dog friendly home

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

About: As a student with a dog of my own, I've gone through numerous rounds of various kind of training! From potty training, to simple basic obedience tr... (more)

8. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"Our dog received the best care imaginable. We received photo updates and it seems the dog's vacation was enjoyed as much as our own. Five stars! (more)"

9. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

6 repeat clients

"Madison was very responsive and sent lots of great pictures! She is very laid back, easy going, and flexible! Will definitely recommend and use again!! Plus,... (more)"

10. Dakota

Pet Lover with Large Fenced Yard!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting

"Dakota and Jen were great with our two small dogs, Teddy and Mojo. They came to our house to meet the dogs and get special instructions for Mojo's diet befo... (more)"

11. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

37 repeat clients

"Kristal was exactly what I was looking for when my husband & I took an extended vacation! I loved that she was around her home most of the time and had a la... (more)"

12. Khat

Pup Nation

South Shore, Chicago, IL, 60637

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

4 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. 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)

14. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Nikki took great care of my very energetic and sometimes hardheaded puppy Zane. She took him on long walks, which he loves. I'm sure Zane had a great time wi... (more)"

15. Martineja

Your dog's new best friend!

Kenwood, Chicago, IL, 60653

Dog Boarding, House Sitting, Doggy Day Care

9 repeat clients

"My dog Bella really enjoyed her stay with Martineja. She kept Bella over the weekend and even offered to pick her up since I live along her normal route home... (more)"

16. 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)"

17. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

3 repeat clients

"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)"

Available this weekend
18. 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)"

19. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

9 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)"

20. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"Jeannette M Tom has been a caregiver for our beagle, Boomer. He walked, talked and ran with him. I trust him with all my pets! (more)"

Experience exceptional service and a personalized match

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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: