Dog Boarding in Woodlawn, Chicago

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

1. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jennifer took care of my Shih Tzu for 3 days over Thanksgiving. My dog was well taken care of..I didn’t have to worry about him. She sent a daily message and... (more)"

2. Jenny Verified Background Check

Dogs bring the best out of me!

Hyde Park, Chicago, IL, 60615

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

"Jenny and Kyle were amazing with my dog :) Leroy had a great time and I could tell he got a ton of extra attention. They were very good about following all o... (more)"

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3. Beverly Verified Background Check

Home full-time, individual care

Chatham, Chicago, IL, 60620

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

"This was my first time leaving my fur baby and I was feeling more than a little anxiety about leaving him with a stranger. Well Beverly put all of those feel... (more)"

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4. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

"Elizabeth and her family took such wonderful care of our 10 month old pup, Bear, while we were away for 5 nights. This was the longest we had ever left him a... (more)"

Confirmed availability
Memorial day
5. Janet Verified Background Check

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Janet was AMAZING with our 15 year old Fifi. Our dog is high maintenance and requires a lot of personal attention. Janet loved on her like she was her own.... (more)"

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6. Tonisa Verified Background CheckRover 101

Your pups second home....

Calumet Heights, chicago, IL, 60617

Dog Boarding, Doggy Day Care

"Can't wait to have Tonisa watch Bentley again. She was great and her kids were wonderful with Bentley. We truly appreciated receiving the pictures of Bentley... (more)"

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7. Dwight Verified Background CheckRover 101

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

Dog Boarding, 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)"

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8. Marga Verified Background Check

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Kali seemed happy and relaxed with Marga and Kate ! She has been in boarding with the vet before, where she came back looking out of it and stressed. But she... (more)"

Confirmed availability
Memorial day
9. Khala Verified Background Check

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

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

"Khala has been so fantastic. On our 2nd time with her I couldnt drop off Major, and she came to pick him up. He was beyond thrilled to see her!! We are so lu... (more)"

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10. Laura Verified Background Check

Dogs are my therapy

Hyde Park, Chicago, IL, 60637

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

"Hello, Laura lived in a garden apartment in my home for a full year, and when I left on vacation for 2 weeks, I left my beautiful dog Bella with her. Laur... (more)"

11. Craig Verified Background CheckRoverGORover 101

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

"Dylan had a great time with Craig!!! He was treated to trips to the dog park and had the company of other dogs during his stay. Craig sent pictures and upda... (more)"

Confirmed availability
This weekend
12. Jill Verified Background Check

I'll run with your dog

Hyde Park, Chicago, IL, 60637

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

"Jill was great. She offers prompt and regular communication. She is flexible and accommodating to various schedules. She and her husband were kind and patien... (more)"

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13. Ashley Verified Background Check

Open heart and open home..

Kenwood, Chicago, IL, 60615

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

"Ashley was amazing with Betsy! We are so happy we found her last minute. (more)"

Confirmed availability
This weekend
14. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

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

"Alicia is so charismatic, fun, and she LOVES animals! Knowing her as well as I have for all these years, I can assure you that any pet is in amazing hands wi... (more)"

15. Fatmah Verified Background Check

I will run with your dog

Kenwood, Chicago, IL, 60615

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

About: Pet loving, flexible, and very active. Love to take your dog for a run or come by your house to take care of your pets. My previous experience with... (more)

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16. Cassidy Verified Background Check

I’ll run with your dog

Hyde Park, Chicago, IL, 60615

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

"Cassidy grew up on a dairy farm and has cared for a variety of animals - from millipedes to cows! She has always lived with dogs and cats and has an uncanny... (more)"

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17. Purvi Verified Background Check

Friendly and nurturing dog lover

Hyde Park, Chicago, IL, 60615

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

"Purvi did a great job taking care of Toby while I was away. She took him on walks and sent me regular updates. I would def use her again! (more)"

18. Wynita Verified Background CheckRover 101Home inspection and phone-screening

Wyn's Happy Paws

Woodlawn, Chicago, IL, 60637

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

"Wynita was super attentive, accommodating and made Cuba feel safe and at home. Also, Wynita made me feel certain that my pet was in great hands. She was supe... (more)"

19. Jenssen Verified Background Check

BEST DOG WALKER ON MY SIDE OF TOWN

South Shore, Chicago, IL, 60649

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

About: Hello, fellow dog lovers! I grew up on a ranch raising cows, chickens, horses, dogs, and other various critters. I was always told I give more to m... (more)

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20. Alex Verified Background CheckRover 101

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Alex did a wonderful job taking care of our dog in his house. He provided lots of updates with photos and was very accommodating. He took great care of our d... (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: