Dog Boarding in 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. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

4 repeat clients

"Belle's first overnight stay. Gerdas was great with her as always. (more)"

2. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

28 repeat clients

"Jessica was definitely a find. She was great to work with, punctual, and organized. We received photos and updates every day we were away and Jessica always ... (more)"

3. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

6 repeat clients

"This was our first Rover.com experience, and Cindy's pic message updates were reassuring. We are so glad to find a caring place so close to home! (more)"

4. Nadia

I'm a vegetarian: I love animals!

Lincoln Park, Chicago, IL, 60614

Dog Boarding, Doggy Day Care, Dog Walking

"Nadia has cared for my pets on numerous occasions, and I recommend her wholeheartedly. She is an animal-lover through-and-through. She clearly creates an emo... (more)"

5. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

1 repeat client

"I would highly recommend Megan. We met before our stay to ensure that our dogs would get along. Megan sent lots of updates during Mini's stay, which was re... (more)"

6. Chris

My wife and I = TOTAL DOG LOVERS!!!

West Town, Chicago, IL, 60622

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

"Chris sent many pictures throughout the stay and Ivy loved playing with Taco. I would definitely recommend them! (more)"

7. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 repeat clients

"Richard was awesome with Cassie and took very good care of her. He updated me regularly and was open when my flight was late in returning. He sent pictures a... (more)"

8. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

1 repeat client

"Gail was so great with my dog, Oliver. I have a pretty clingy shih tzu and after trying two sitters for him, I thought we just couldn't leave him alone anymo... (more)"

Confirmed Holiday Availability
9. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

19 repeat clients

"Magdalena did a wonderful job. Coop was happy and well taken care of. She loved play time with the other pups and Magdalena even worked with her on training ... (more)"

Confirmed New Years Availability
10. Madeleine

Reliable, friendly & flexible!

Near West Side, Chicago , IL, 60607

Dog Boarding, Drop-In Visits

1 repeat client

"Madeleine was so great! She sent a lot of pictures and updates throughout each day and George came home super happy and tired ?. I will definitely be sending... (more)"

11. Alexandra

Crazy Dog Lady

West Town, Chicago, IL, 60612

Dog Boarding

4 repeat clients

"Alexandra was amazing!! I could tell both her and Cooper had a fantastic week while I was gone and I couldn't have asked for more. She sent me updates, was v... (more)"

12. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

1 repeat client

"Sara's awesome! Winston loved her. 100% recommend her if you're looking for someone to watch you dog. (more)"

13. Andrew

A Dog-Loving New Lawyer

Loop, Chicago, IL, 60604

Dog Boarding, Drop-In Visits, Dog Walking

7 repeat clients

"Andrew saved the day when my regular dog sitter had to go out of town mid-way through my business trip. They did a great job of coordinating the exchange, an... (more)"

14. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

About: I have owned a dog walking company in LA for over 10 years and we are still going strong. I am looking forward to walking in dogs in my home town. ... (more)

Confirmed Holiday Availability
15. Julia

LOVING mom to watch your dog!

Near West Side, Chicago, IL, 60612

Dog Boarding, Doggy Day Care, Dog Walking

About: My daughter and I have a 6 year old Shorkie that we have had since she was a puppy. I grew up with dogs and am an animal lover and advocate. I be... (more)

16. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

5 repeat clients

"So friendly and flexible with details! She took amazing care of my pup! Would recommend her to anybody and will for sure use Betsey in the future!! (more)"

17. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

5 repeat clients

"I'm so thankful that we now have a reliable, flexible and caring dog sitter! Samantha and John were great from the first meet and greet and pictures througho... (more)"

18. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

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

"Samantha is a responsible, caring, genuine person with a big love for dogs. I know Samantha would show love and affection to any animal that she comes across... (more)"

19. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

18 repeat clients

"Elesha was a great sitter for Wyatt and super amenable to our last minute booking. Our dog requires medication twice daily and she was very conscientious abo... (more)"

20. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

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

1 repeat client

"It was our first experience leaving our dog for more than a day and definitely Samantha was awesome and great. She replied almost immediately and she was alw... (more)"

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Learn About Premier

Dog owners love Rover's Chicago dog sitters. 9,532 owners have reviewed sitters in the Chicago metro area, giving them an average rating of 5/5. Browse profiles, read reviews, and check us out on Yelp.

Wondering how much you can expect to pay for a night on Rover.com? Check out our average dog sitting rates to get an idea before you start a conversation with a sitter.

Home to the largest number of highways in the nation and second busiest airport in the world, Chicagoans are travelers as much as they are dog lovers. That's why, when preparing for a trip, Chicago dog owners want nothing but the most loving home for their dogs while they're away.

With Rover.com, that gets a little easier. Scroll through our selection of loving sitters, click on a listing you like, and start a conversation. From Hyde Park to Wicker Park, Rover.com sitters have access to the Windy City's only off-leash, dog-friendly areas, where dogs can play freely and recharge with special, dog-level drinking fountains and separate areas for shy pets to unwind.

You love your dog. We love your dog, too. How much? We'd love to show you. Book dog boarding, pet sitters, and dog walking in Chicago on Rover.com, and stop by our blog to see what we're all about.

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 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 nonprofits across the U.S., including: