Dog Boarding in Woodlawn, Chicago

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

Confirmed availability
 Easter weekend
1. Dionne Verified Background CheckRover 101

Furry Friend Extraordinaire!

Woodlawn, CHICAGO, IL, 60637

Dog Boarding, Doggy Day Care

"Dionne is great with Moose! Updated is a lot with awesome pictures on his walks. We love that she would take Moose to the lakefront on his walks. We know he wa… (more)"

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2. Pamela Verified Background Check

Dogs are four legged best friends

Grand Boulevard, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Super responsive and easy to work with - thank you! (more)"

Confirmed availability
 Easter weekend
3. Shekinah Verified Background Check

flexible schedule & a big yard

Chatham, Chicago, IL, 60619

Dog Boarding, Doggy Day Care, Dog Walking

"Shekinah was a excellent host for our dog. Our dog was well taken care of and shekinah separated our dogs even though I thought Nova would get along with her d… (more)"

Confirmed availability
 Easter weekend
4. Elizabeth Verified Background Check

Animal lover active animal activist

South Shore, Chicago, IL, 60649

Dog Boarding, Drop-In Visits, Doggy Day Care

"She’s great nothing more, nothing less my new born puppy came home in better condition than Elizabeth picked her up in. Your dog will be entertained and well t… (more)"

Confirmed availability
 Easter weekend
5. Valerie Verified Background Check

Animal lover with a heart of gold!

South Shore, Chicago, IL, 60649

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

"I picked Valerie because of her impeccable reviews and her proximity to my home and I was blown away by her professional care for my dog. Each day i was given … (more)"

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6. Mariam Verified Background Check

I am Home full-time, flexible hours

New City, Chicago, IL, 60609

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

"Everything was great!! She sent me pics of Zoey. Zoey was so tired from playing, she went right to sleep when we got home. Definitely will use her again!! (more)"

Confirmed availability
 Easter weekend
7. Tonisa Verified Background CheckRover 101

Your pups second home....

Calumet Heights, chicago, IL, 60617

Dog Boarding, Drop-In Visits

"Tonisa was an excellent dog sitter. She took us at the last hour because our other dog sitter had an emergency. Tonisa provided us with pics and updates thro… (more)"

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8. Beverly Verified Background Check

Home full-time, individual care

Chatham, Chicago, IL, 60620

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

"Beverly was a fantastic and enthusiastic person to board my dog with. She met with us a few days before the boarding, so the drop off was seamless. Beverly had… (more)"

9. E Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

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

"Elizabeth was wonderful. She kept me updated about Mary(my dog) through out the stay. I added pick up and drop off service and she was very flexible and unders… (more)"

10. Anthony Verified Background Check

Pilsen Dog Walker/Cat Sitter!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting

"Anthony is SUCH a nice person, and you can tell he loves dogs. He sent plenty of photos during the stay. I will not hesitate to book with him in the future. (more)"

Confirmed availability
 Easter weekend
11. Aaliyah Verified Background Check

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

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

"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 with … (more)"

Confirmed availability
 Easter weekend
12. Maria Verified Background CheckRover 101

Your Loved One's Second Home

Loop, Chicago, IL, 60605

Dog Boarding

"This is the second time Maria has watched my dog Peanut while I was out of town and she surpassed my expectations again. She was in constant communication with… (more)"

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13. Christopher Verified Background Check

Dog loving couple in South Loop.

Near South Side, Chicago, IL, 60605

Dog Boarding, Drop-In Visits

"Christopher and his girlfriend were awesome! Prompt responses and great to work with when I had to leave town on short notice - would definitely recommend and … (more)"

14. Leslie Verified Background Check

Extra love to give

Woodlawn, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Doggy Day Care

"She's amazing with my babygirl, and that's why I will continue to use her service's for caring for my pooch (more)"

Confirmed availability
 Easter weekend
15. Matt Verified Enhanced Background CheckRover 101

4 parks within walking distance!

Armour Square, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Matt was great! I appreciated his thoroughness and requiring a meet and greet prior to arrival to make sure it was a good fit all around. Very flexible and ea… (more)"

Confirmed availability
 Easter weekend
16. Jasmine Verified Enhanced Background Check

Plenty of long walks and treats!

Bridgeport, Chicago, IL, 60609

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

"Willis and I LOVE JASMINE!!!!! We started initially with a play-date and I had a really great feeling about jasmine and her watching my babe. Throughout my out… (more)"

17. Darcy Verified Enhanced Background Check

Ace Ventura for pets 🐶😻

Loop, Chicago, IL, 60605

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

"Darcy is the BEST!! We totally trust her to take amazing care of Milo whenever we’re out of town. She plans lots of fun activities for him and keeps him active… (more)"

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18. Jonathan Verified Background Check

Your dog is my dog!!

Near West Side, Chicago, IL, 60607

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

"Jonathan was great. He treated Jax as if it was his own. I felt comfortable leaving Jax with Jonathan I knew he was in good hands. Jonathan is my go to dog si… (more)"

Confirmed availability
 Easter weekend
19. David Verified Enhanced Background Check

NOT JUST A PET BUT FAMILY

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Doggy Day Care

"It is such relief knowing your pet will be taken care of in the best hands by David. He kept me updated on how Sam is doing knowing he was a rescue Doberman p… (more)"

20. Janet Verified Background Check

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Janet is the greatest! She loves dogs and takes care of them like they’re all her own! My dog loves his visits and his dog friends he’s made there! (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: