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.
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1. Amanda

I'm a student and I love dogs!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Amanda was a joy to have keep our pup. He takes a moment to warm up but Amanda was able to build trust with him and before you knew it...she was giving him ... (more)"

Confirmed Holiday Availability
2. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

8 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)"

3. 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)"

Confirmed Holiday Availability
4. 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)"

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. 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)"

7. 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)"

8. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

9 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)"

9. 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)

Confirmed Holiday Availability
10. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

10 repeat clients

"Lynnettra was flexible with drop-off and pick-up time, and her response time was excellent. Our pup got along well with her dogs and appeared to have a blast... (more)"

11. Lauren

Puppy paradise-across from big park

Grand Boulevard, Chicago, IL, 60615

Dog Boarding, Drop-In Visits

About: My boyfriend and I LOVE dogs and would love to have yours come and stay with us! We have been dog foster-parents for two years and now have an 8 mo... (more)

12. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"I was thoroughly please with Ebonee' s skills as a dog sitter, because she went beyond my expectations. Having her as my pet's sitter allowed me to enjoy m... (more)"

13. Susan

I love to run + chill with dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

2 repeat clients

"Susan did a great job taking care of my Cohiba! I would definitely book w/her again. She gave me daily updates and sent me pics to assure me he was doing wel... (more)"

Confirmed Holiday Availability
14. 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)"

15. Hanna

I will give your dog/s lots of hugs

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"I have known Hanna her entire life and what I have observed is what a loving and compassionate person she has grown up to be. She loves animals and is patien... (more)"

16. Sean

"A dog's best friend"

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Sean is a very responsible, impersonal and pet-friendly guy who loves animals! He's had a lot of experience with walking and taking care of dogs since we fre... (more)"

17. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"We love them! Kimberlie kept me updated with my doggy every day while I was in Europe. She kept me in the loop on how my doggy slept, ate and how his overall... (more)"

18. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

4 repeat clients

"Rebba was awesome!! I received pics and videos of my fur baby throughout the weekend (allowing me to relax and enjoy myself) and when I picked him up, it too... (more)"

19. 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)"

20. 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)"

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: