Dog Boarding in Chicago

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

1. Tim

Love dogs and the Loop

Loop, Chicago, IL, 60601

Dog Boarding

2 repeat clients

"Tim was a great sitter and I'll definitely be reaching out to them next time my pup Nala needs a sitter. He was quick to respond when I reached out last minu... (more)"

2. Chris

My wife and I = TOTAL DOG LOVERS!!!

West Town, Chicago, IL, 60622

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

1 repeat client

"Such a nice couple!!! I was in a total bind to leave town last minute and they were so accommodating and helpful in getting my pup taken care of. Their dog i... (more)"

3. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

7 repeat clients

"Cindy was so great with Koda! She sent lots of updates & made him feel right at home! We are definitely hoping that she will watch our little pup again next ... (more)"

4. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 repeat clients

"Great stay! Quickly responded to any questions or messages, very accommodating for drop off and pick up times, I got lots of updates and can tell my pup had ... (more)"

5. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

3 repeat clients

"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)"

6. Christi

Old Town Puppy Lover!

Near North Side, Chicago, IL, 60610

Dog Boarding

1 repeat client

"Christi is the best. I've been using Rover for four years and I have to say that Christi is my favorite sitter - after just one experience! She's SO communic... (more)"

7. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

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

1 repeat client

"Excellent sitter! Samantha is prompt, responsible, and committed. I am very satisfied. She is always welcome to look after my dog. (more)"

8. Grace

Peace. Love. Dog Treats.

Loop, Chicago, IL, 60605

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

1 repeat client

"Grace was super nice and very understanding - we were leaving our Stormy in the late evening with her plus with a very short notice. I will definitely contac... (more)"

9. Julia

LOVING mom to watch your dog!

Near West Side, Chicago, IL, 60612

Dog Boarding, Doggy Day Care, Dog Walking

"Julia and Tammy were amazing were our dog, Roger. He was taken to the dog park and even came home with a new toy he claimed as his own there! He was exhauste... (more)"

10. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

6 repeat clients

"Great stay for Tio. He had plenty of walks and fun with doggie day care visitors. Nice location near a park. Back yard available for scratching his back wi... (more)"

11. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

29 repeat clients

"Wow! I should have done this a lot sooner! I thought I did, but I guess I forgot! Anyways, Jessica is amazing and was wonderful with Millie. Millie can be sc... (more)"

12. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

5 repeat clients

"Gerda was great!! She was so sweet and calm about Sierra's medicine and ear-cleaning needs. It was a long trip (2 weeks) and she regularly sent me pictures,... (more)"

13. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

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

"Meryl was the perfect sitter for our dog who suffers from separation anxiety. I am so thankful that I found her and will certainly use her again. (more)"

14. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"Tatiana was great with my dog Lucy. She was accommodating to our travel situation, concerned when Lucy was not eating because of some anxiety she experienced... (more)"

15. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

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

3 repeat clients

"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)"

16. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

6 repeat clients

"Toby had a great time with Betsey and I could enjoy my vacations knowing that my puppy was good. I got a lot of pictures and messages everyday. I will recomm... (more)"

17. Derick

Any dog is the best kind of dog

Near West Side, Chicago, IL, 60607

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

"Derick is a great guy that's very experienced and knowledgeable about dogs. I would trust and recommend him anytime in the future. Take a leap of faith and b... (more)"

18. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

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)

19. Jenna

love and care for all dogs

Loop, Chicago, IL, 60605

Dog Boarding, House Sitting, Doggy Day Care

About: I had a dog when I was younger so I know what it's like to take care of a dog. I enjoy being active and taking dogs on walks would be very enjoyabl... (more)

20. Jessica

Fun and energetic dog sitter!

Lower West Side, Chicago , IL, 60608

Dog Boarding, Dog Walking

2 repeat clients

"Our dog Ollie loves staying with Jessica. He's a repeat house guest, and he gets along great with Jessica's dog Mia. Jessica is also very easy to work with a... (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: