Dog Boarding in Woodlawn, Chicago

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

Confirmed Memorial day Availability
1. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Thank you Nina! I was so nervous about this process. You made it so comfortable for me and my family!!! Thank you for the updates and the photos and most imp... (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

4 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. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

12 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)"

Confirmed Memorial day Availability
4. Dakota & Jennifer

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

39 repeat clients

"Fantastic stay with Dakota and his mom. Riley, my beagle, looked so happy when I picked up him. It's a warm home with a nice secure backyard. Also really ap... (more)"

5. 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)"

6. Katie

dog-loving student

Hyde Park, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

"Katie was a perfect dog sitter for us! She was very professional, friendly, and seemed to sincerely enjoy looking after both of our dogs. She kept us informe... (more)"

7. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

13 repeat clients

"Kali seemed happy and relaxed with Marga and Kate ! She has been in boarding with the vet before, where she came back looking out of it and stressed. But she... (more)"

Confirmed Memorial day Availability
8. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

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

"Dwight has done a wonderful job with my dog and my best friends dog when he offered to take them both at short notice. The dogs loved him and he sent a phot... (more)"

9. Lillian

Flexible Schedule - Loves to walk!

Hyde Park, Chicago, IL, 60637

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

"Lily was great with TJ and provided really excellent service. She checked in with me at several points through TJ’s stay to let me know how he was doing. Thi... (more)"

10. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"I recommend Alex to be a Dog walker and sitter on Rover since he is very punctual and always keeps his commitments. I am sure he will take great care of any ... (more)"

11. Khat

Pup Nation

South Shore, Chicago, IL, 60637

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

5 repeat clients

"I am so grateful that MJ and Egypt were able to stay with Khat. I unexpectedly needed the service and she responded and the stay was book the same day. She w... (more)"

12. Jennifer

I will love your dog as my own.

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

1 repeat client

"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)"

13. Dena

Doggy Spoiler Alert

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits

19 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)"

14. Samantha + Mac

Looking for new friends!

Hyde Park, Chicago, IL, 60615

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

"If you are looking for a great couple to watch your pet, then Samantha and Mac are your people! This was my husband and I’s first time leaving our dog and we... (more)"

Available this weekend
15. 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)"

Confirmed Memorial day Availability
16. Amanda

Uchicago student who loves dogs!

Hyde Park, Chicago, IL, 60637

Dog Boarding

3 repeat clients

"Amanda was great with our puppy, Rudy! Rudy is 4 months old and can be a little ball of energy, so Amanda's flexible schedule was great. She sent us pictures... (more)"

Available this weekend
17. 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)"

18. Krista

Flexible schedule, love dogs

Hyde Park, Chicago, IL, 60615

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

About: Other dog owners describe me as a caring, responsible, loving dog lover and pet sitter. I'm a current grad student so I have a flexible schedule to... (more)

Available this weekend
19. Shawn

I'll show your dog what love is.

Grand Crossing, Chicago, IL, 60637

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

3 repeat clients

"Shawn took excellent care of our dog Koffee. She warmed up to Shawn quickly. When Koffee was not acting her normal self, Shawn was great with communicating w... (more)"

20. 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)"

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: