Dog Boarding in Woodlawn, Chicago

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

1. Brandilyn

Dog Lovers With Fun Doodle

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care, Dog Walking

"Brandi and Andy were fantastic hosts to our dog Timon, and get our highest recommendation. Timon was very happy when we picked him up after a weekend full of... (more)"

2. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Breana is great! Our dog, Ginger, boarded with her for five days: Breana took the time to meet us and Ginger beforehand, she sent photos to update us through... (more)"

3. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care, 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)"

4. 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)"

5. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Drop-In Visits, Doggy Day Care

8 repeat clients

"Samantha was great to work with, and her own dog, Waffles, is very cute and friendly. Samantha took careful notes about our pup's schedule, habits, and medic... (more)"

6. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

"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)"

7. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 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)"

8. Nellie

Graduate student who loves dogs :)

Near South Side, Chicago, IL, 60616

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

"Nellie was great! She helped us out when we were in a pinch, and gave Rudy a great vacation while we were away. She gave frequent updates, and when our pup h... (more)"

9. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

34 repeat clients

"Krystal and her family were absolutely wonderful with the Fab Four - they were also great whenever I wanted to come over to see the dogs. I highly recommend ... (more)"

10. 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)

11. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

3 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)"

12. 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)"

13. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

"Lynettra was awesome! She took great care of teddy and even gave him a bath! Will be booking again for sure! (more)"

14. 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)"

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

1 repeat client

"Brandy took Zoey in for a last minute weekend stay and was very flexible with pick-up and drop-off times. She has a great space for dogs with a nice sized fe... (more)"

17. 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)"

18. Shellie

Love dogs, owned them for years

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care

"My Pooch was so spoiled during his stay with Shellie...he was so well-taken care of. He's a fiery minpin so I was a little nervous about how he would be wit... (more)"

19. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ❤THEM

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)

20. 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)"

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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: