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. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

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

"Dwight was an amazing host for our little buddy Arthur! He was communicative and flexible in drop-off and pick-up times, and sent some lovely photo and text ... (more)"

2. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

"Saran was the BEST dog sitter ever! My Cooper fit right in with the other dogs in her home and she made sure he was comfortable! I was updated with pictures ... (more)"

3. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"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)"

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4. 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

"Alex did a great job boarding my very energetic dog, Gertie. He was flexible, responsive and sent a bunch of great photos. We got back very late so he brough... (more)"

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5. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

"Bob went above and beyond to make sure that our dog was comfortable and happy. He spent a lot of time with her, taking her on more walks than we asked and ev... (more)"

Confirmed availability
4th of July
6. Jen & Dakota

Large Fenced Yard and House!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"Dakota and Jen were very attentive to Biscuit’s needs and made his acclimation to their home very comfortable. They checked in daily to let us know how thin... (more)"

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7. Susan

I love to run + chill with dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"What an amazing stay! Susan really saved me with the last minute booking, and was wonderful with my husky, Watson. She gave him walks and love and even sent ... (more)"

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8. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

"Kat is very good dog sitter. My big boy Arrow looks very happy with her. She took him out for a long walk every day! I really want Arrow to continue stay wit... (more)"

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9. Jennifer

I will love your dog as my own.

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

"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)"

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10. Beverly

Home full-time, dog park membership

Chatham, Chicago, IL, 60620

Dog Boarding, Doggy Day Care

"Beverly was wonderful with my two fur babies! I got picture updates of my dogs looking so at home and relaxed. Plus, Beverly followed my care instructions to... (more)"

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11. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"oli loved his stay. marga and kate were so wonderful and patient w oli. he looked so content and cozy in the pics we got. i would 100% recommend and rebook! (more)"

12. Joy

Your Dog Will Be Loved!

South Shore, chicago, IL, 60610

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

"Joy is the sweetest and most caring person I have met! She is a natural with dogs and they are just drawn to her and love her! (more)"

Confirmed availability
4th of July
13. Jenisa

pet lover who works from home

South Side, Chicago, IL, 60653

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

"Jenisa was amazing. Very communicative and kept me updated on how my baby was doing. I know my dog had a blast staying with her! Defiantly found a permanent ... (more)"

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14. Ashley

4-5 walks/Day & I Work from Home!

Hyde Park, Chicago, IL, 60637

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

"Ashley took really good care of my Roo. She took him out for a walk even when it was rainy! She asked me where he usually sleeps. She let Roo sleep in her... (more)"

Confirmed availability
4th of July
15. Rosa

Experience with Geriatric Dogs

South Shore, CHICAGO, IL, 60649

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

"Rosa is a wonderful pet owner. She calls her pets, the kids. She loves her dogs and makes sure they are well-taken care of, for example, when her dog was dia... (more)"

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16. Danielle

All-Day Care for Your Doggo

Hyde Park, Chicago, IL, 60615

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

"I have known Danielle all her life , she has looked after my dog on numerous occasions . Danielle is trustworthy, reliable , friendly and caring she loves do... (more)"

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17. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Ebonee was very friendly and accommodated me on very short notice. I highly recommend acquiring her services. She updated me with photos and my dog was very ... (more)"

18. Krystal

Krystal Loves the Pups

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Working with Krystal was an excellent experience. She took great care of our dog and was easy to communicate with before and during the stay. Would definitel... (more)"

Confirmed availability
4th of July
19. Khat

Pup Nation

South Shore, Chicago, IL, 60637

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

"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)"

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20. Jade

Home all day to stay with your pup!

Hyde Park, Chicago, IL, 60637

Dog Boarding

"She is awesome... I'm pretty sure my dog liked being at her place more than he likes being home ? She keep me updated with pictures and was supper flexible w... (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: