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. Noreen

Loving and fun dog sitter!!

Beverly, Chicago, IL, 60643

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

22 repeat clients

"Greta was very well cared for by all host family members. Noreen worked with Greta to make her feel more comfortable in strange surroundings. Greta was wip... (more)"

2. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

"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)"

3. Maribel

M & B Doggy B & B

Chicago, IL, 60632

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

6 repeat clients

About: Woof woof! My name is Maribel and when I am not spending time cuddling with my favorite four legged friends (or my two legged live-in boyfriend, Br... (more)

4. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

1 repeat client

About: A lifetime of experience with multiple dogs and friendly felines, I love both and am here to provide loving care and attention to your furry pet wh... (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. 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)"

7. 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

"Let me start by saying that I was thoroughly please with Duff care while I was gone, Breana took great care of my little one who was reluctant at first and ... (more)"

8. Samantha

Your dogs STAYcation spot!

Gage Park, Chicago , IL, 60632

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

4 repeat clients

"Samantha was awesome! She watched my two pups over the holiday break and she did an incredible job. She met the dogs in advance and asked about any special... (more)"

9. 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)"

Available this weekend
10. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Drop-In Visits

2 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)"

11. 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)"

12. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

About: Hi all, my name is Kimberlie and I have grown-up with dogs & truly just love all different sizes & personalities!! Life is better with a pooch :) W... (more)

13. 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)

14. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"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)"

15. May-May

May-May Chen, Student at UChicago

South Side, Chicago, IL, 60615

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

About: **About me** Hello! My name is May-May and I live in Hyde Park with my 2 roommates. I just recently graduated from the University of Chicago, but... (more)

16. 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)

17. 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)"

18. Rebecca

Active, fun, and making them happy

Kenwood, Chicago, IL, 60615

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

1 repeat client
No Reviews Yet

About: I have lots of experience with dogs and pets. I have been walking dogs for more than 10 years and have done cat and dog sitting. I am happy when ... (more)

19. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

About: I'm an owner of a playful energetic nine year old boxer. Whenever you see me, you're sure to see my dog Marley. I'm very active so dogs usually ti... (more)

20. Ericka

Your Dog is My Bestfriend

Hyde Park, Chicago , IL, 60615

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

"I am very interested that ericka is deciding to work with rover. She is amazing when it comes to Animals , she loves them. She will literally sit there and p... (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: