Dog Boarding in Grand Boulevard, Chicago

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

1. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

1 repeat client

"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)"

2. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

"My dog Rizzo is my child and I wouldn't trust her with anyone else besides Megan. As an avid dog mom herself, Megan doesn't just puppy-sit, she extends her h... (more)"

3. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

3 repeat clients

"Marga did such a wonderful job with our pup! We were out of town for almost 5 days and she attentively cared for our dog and sent regular updates. Our dog, L... (more)"

4. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

"Sara has taken care of my 2 Maltese poodles several times. She has stopped in to feed and walk them when we are unable to get home from work on time as well... (more)"

5. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

5 repeat clients

"Betsey is awesome. Our dog has stayed with her twice and her third stay is already booked!!!! Our dog loves staying with Betsey as made her feel right at ho... (more)"

6. 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)"

7. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

5 repeat clients

"Samantha was great to work with, and her own dog, Waffles, is very cute and friendly. Samantha took careful notes about our pup's schedule, habits, and medic... (more)"

8. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 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)"

9. Mireya

I'm very active & love to rockclimb

Near West Side, Chicago, IL, 60607

Dog Boarding

"She did an excellent job. She gave updates whenever asked with no hesitation and was very friendly and helpful from the start. Ralph seemed to have a very go... (more)"

Confirmed Holiday Availability
10. Christi

Dog Lovers in the Loop

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"I cannot rave enough about Christi and her husband! They were a fantastic duo that made sure Miley was well taken care of during her stay in their home. It c... (more)"

11. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

"Martin was amazing with my little chihuahua Earl! He sent updates everyday, both pictures and short texts, about how my dog was doing, what he was eating, if... (more)"

12. Keeshina


Grand Crossing, Chicago, IL, 60619

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

About: Hi , My name is Keeshina As a kid Me & my sisters Loves any pet we come in contact with!! My sis has 2 pits 2 cats other a Lil tea cup! I ha... (more)

Confirmed Thanksgiving Availability
13. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"We're about to take our first trip away from our puppy Duncan and were nervous about finding him a place to stay while we're gone. We left him with Bradley ... (more)"

14. Dana

Hyde Park Animal Sitter for Hire!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

2 repeat clients

"Dana was extremely nice, kind & professional. I would take Macky back to Dana any time. (more)"

15. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

7 repeat clients

"Bella's stay with Danielle was excellent!! She sent plenty of photos and updates. Very flexible with pick and drop of arrangements. Danielle is extremely per... (more)"

16. Dawn

Choose Dawn! I'm not JUST a soap..

Grand Boulevard, Chicago, IL, 60653

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

2 repeat clients

About: I believe about half of my heart is filled with my love for dogs, the other have is Johnny Depp and Mac and cheese! I've taken care of about 20 dog... (more)

17. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was amazing!!! By the looks of the pictures, our dog enjoyed his stay! She sent updates about twice a day which was great! I was glad I left him in the... (more)"

18. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

About: In our house, pets are a part of the family. People with busy schedules should still be able to enjoy the love and companionship of a dog. I have... (more)

19. Hika

Your Dog will be Loved by our Family!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"Hika is amazing! I left my corgi at her place for about 10 days. Many sitters aren't willing to take Ruby for so long, and Hika was able to help last minute.... (more)"

Confirmed Thanksgiving Availability
20. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was able to care for my miniature pinscher when I went to Indiana for a family reunion. She fed him, walked him twice a day, then checked on him three... (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 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, 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, 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, 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: