Dog Boarding in Woodlawn, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Dismiss
1. Maribel

M & B Doggy B & B

Chicago, IL, 60632

Dog Boarding

7 repeat clients

"Maribel and Bryan were amazing hosts for Donnie! From the minute we met them, we knew they would take care of him as if he was their own. They were extremely... (more)"

2. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"Rebba was amazing! She took such great care of my dog while I was away on a trip. It's really hard to come by sitters who don't stereotype all pitbulls. She ... (more)"

3. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

4 repeat clients

"It goes without say that I would recommend Bob to anyone looking for a caring, knowledgeable, reliable dog sitter. Bob was flexable to my changing schedule, ... (more)"

4. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

3 repeat clients

"Saran sent us pictures and kept us updated on the status of our dogs! Communication was great and our doggies enjoyed their stay with Saran and her doggies. ... (more)"

5. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Courtney watched my 3 year old Yorkie-Dachshund mix and was great! She was flexible and patient with my frequent change of travel plans and made me feel comf... (more)"

6. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"Kimberlie is fantastic! She sent me picture updates and took care with every detail. She has been flexible and generous. Her little guy, Ollie, is laid ba... (more)"

7. Manon

Full time- I'll run with your dog!

South Chicago, Chicago, IL, 60617

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

1 repeat client

"Manon was excellent with charlie, he had an amazing time with her, she is very understanding, compassionate, we had to extend our trip for other reasons and ... (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)"

Available this weekend
9. Damien & Angela

Home full-time with a fenced yard

Chicago Lawn, Chicago, IL, 60629

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

"Damien has an absolute love for all animals, especially dogs! He shows such a passion for every breed and size of dog. As a matter of fact, he loves to call... (more)"

10. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

4 repeat clients

"Madison and her family were wonderful hosts to my dog! (more)"

Available this weekend
11. 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)"

12. 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)

13. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

7 repeat clients

"Marga took care of both my dogs Max and Nala during last weekend. I am 100% happy with her. She was extremely attentive to the instructions I gave (I am a bi... (more)"

14. 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)"

Available this weekend
15. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

About: My goal as your local pet-sitter/ dog- walker is to raise extra income within my household along with doing something I absolutely love! I'm also l... (more)

16. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"Paige watched Portia while we were away for a long weekend. We came back to a happy dog who clearly had enjoyed her time with Paige! Paige sent lots of photo... (more)"

17. 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)

18. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

"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)"

19. George

Travel anytime to see your dog!

Kenwood, Chicago, IL, 60605

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

About: I've had dogs (and other pets) all my life, so I know the kind of love and attention that all animals need! I have quite a bit of flexibility durin... (more)

20. Sandra

Long walks on the South Shore

South Shore, Chicago, IL, 60623

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

About: I have cared for my pet dogs ever since I was 10 years old, so I have about 15 years of experience living with dogs. In the past 3 years I have gai... (more)

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: