Dog Boarding in Woodlawn, Chicago

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

Active and Accepting Requests (incl. from Essential Workers)
1. Dionne Verified Background CheckRover 101

Furry Friend Extraordinaire!

Woodlawn, CHICAGO, IL, 60637

Dog Boarding, Doggy Day Care

"Dionne is an excellent sitter! She was very thorough tailoring to my dog Penny's needs, professional and prompt in communication, easy and flexible when sche... (more)"

2. Kathleen Verified Background Check

Some of the best people I know...

Kenwood, Chicago, IL, 60615

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

"Kathleen was great! We had a very unique and stressful situation and she came in at the last minute and saved the day for us. Our pup couldn't have been in b... (more)"

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3. Shaley & Melissa Verified Background Check

Friendly petcare by med student duo

Hyde Park, Chicago, IL, 60615

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

"Very communicative and easy to arrange drop off and pick up. Maggie was in good hands and Shaley sent me several picture updates throughout the weekend. Woul... (more)"

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4. Dwight Verified Background CheckRover 101

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

"This review is very long over due! Dwight and his wife took exquisite, loving care of my Bentley who typically has anxiety. I have always been so worried a... (more)"

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5. Janet Verified Background Check

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Janet was amazing! So great with my dog (who can be difficult sometimes). Winston loves the toy she sent us home with. She was loving, caring and kept me upd... (more)"

Active and Accepting Requests (incl. from Essential Workers)
6. Gabriel Verified Background CheckRover 101

Will be cared for like family

Hyde Park, Chicago, IL, 60637

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

"I think Gabriel knew Rubí (my beautiful dog) better than me. No even joking, to the point that every time he noted some mood change in Rubí, he always contac... (more)"

7. Tonisa Verified Background CheckRover 101

Your pups second home....

Calumet Heights, chicago, IL, 60617

Dog Boarding

"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 th... (more)"

8. Beverly Verified Background Check

Home full-time, individual care

Chatham, Chicago, IL, 60620

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

"My dog is very picky about people, and has no problem being physically or verbally upset when she doesn’t like someone. Therefore, it was very telling that N... (more)"

9. Indy Verified Background Check

Let me love your dog!

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

"Indy was sooooo great with Baxter. She updated me with pictures and videos during my 5 day vacation. It was my first time ever using Rover and Indy walked me... (more)"

10. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

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

"Elizabeth was amazing!!! This is the first time I have ever left my two dogs with a sitter in 10 years. We most recently lost Buffie and Vinnie's brother, Gi... (more)"

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11. Stanley Verified Background Check

My husky loves energetic friends!

Hyde Park, chicago, IL, 60637

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

About: I have been a dog lover since I could remember! I have had dogs ranging from a small chihuahua to a large cane corso. I currently have a Siberian H... (more)

Active and Accepting Requests (incl. from Essential Workers)
12. Matt Verified Enhanced Background CheckRover 101

4 parks within walking distance!

Armour Square, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Matt took great care of my dog. She is a very large dog and reactive on leash, but Matt was comfortable with the breed and asked all the right questions to ... (more)"

13. Elliott Verified Background Check

Marketer by day, Dog lover 4 Life!

Washington Park, Chicago, IL, 60609

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

"Elliot was great! My Black Lab Lucy had a wonderful time with him when we were gone for a couple of weeks. She got lots of walks, playing fret , lots of att... (more)"

14. Ashlea Verified Enhanced Background Check

Lover of all animals! Flex schedule

Near South Side, Chicago, IL, 60605

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

"Ashlea always does a great job taking care of my dogs, and they love her! I highly recommend her to walk or take care of your dogs. (more)"

Active and Accepting Requests (incl. from Essential Workers)
15. Jaya Verified Background Check

Patient & fun dog sitter, Hyde Park

Hyde Park, Chicago, IL, 60637

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

"Jaya takes such loving care of my dog Arthur. She takes him on long walks and ensures he is stimulated. She sends frequent updates with adorable pictures of ... (more)"

16. Katja Verified Background Check

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

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

About: I have cared for dogs my entire life working as a foster parent for multiple organizations including Eye on the Sparrow and AARF. Currently, I have... (more)

17. 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 wit... (more)"

18. Kyle Verified Background CheckRover 101

Over a decade of experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Drop-In Visits

"Kyle and Ben were great! Our dog loves them and seems to have had a great time with their dogs and cats. Kyle and Ben board many dogs in our neighborhood and... (more)"

Active and Accepting Requests (incl. from Essential Workers)
19. Kayla Verified Background Check

Dog enthusiast, trustworthy🐶

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care

"Kayla was great with Teddy, she cared for him as if Teddy was her dog. Kayla sent updated pictures making me feel very comfortable that Teddy was in great ca... (more)"

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20. Saran Verified Background CheckRover 101

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding

"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)"

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: