Dog Boarding in Douglas, 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 took care of both my dogs Max and Nala during last weekend. I am 100% happy with her. She was extremely attentive to the instructions I gave (I am a bi... (more)"

4. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

5 repeat clients

"Cindy was awesome! Took great care of Negroni and always kept me updated with pictures and videos! Made my time away from my baby go by very fast! (more)"

5. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

"Aside from being the huuuuuge dog-lover that Sara is... she is overall the most caring, thoughtful, and responsible person I know. She grew up with her famil... (more)"

6. 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)"

7. 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)"

8. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

5 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)"

9. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Magdalena was so amazing with Sarge while I was away. She kept me updated on him and he seemed happy and tired when I returned. We will certainly be seeing h... (more)"

10. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"Lauren was the absolute best! She was responsive, sent regular updates, and made me feel as comfortable as if I would've left him with my parents! Bentley to... (more)"

11. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

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

7 repeat clients

"Great first experience! Brittany kept in touch daily and sent pics. Juniper was right at home and made new besties including Arro the Pomeranian! Will be us... (more)"

12. Abi

Our home is your dog's home!

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

About: My husband and I love dogs! We've both grown up babysitting and loving dogs but never having one of our own. We think they're great pals for advent... (more)

13. 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
14. 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)"

15. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

"5 stars for Martin! Martin took great care of my dog Guthrie over an extended 8-day overnight boarding stay. From the time we spent together I was convince... (more)"

Confirmed Thanksgiving Availability
16. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"Thanks again Bradley! Bouna loved hanging out at your house with Bolt and Apollo. He laid next to the door and whined for awhile when you dropped him off. ... (more)"

17. Andrew

A Dog-Loving New Lawyer

Loop, Chicago, IL, 60604

Dog Boarding, Drop-In Visits, Dog Walking

4 repeat clients

"Andrew was responsive, friendly, and prompt. Our goldendoodle Bear had a great stay and came home very happy! Would definitely recommend him! (more)"

18. 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)

19. 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)"

20. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"Elesha was really just a perfect sitter for our puppy. She sent us constant updates on their activities with pictures which was such a nice treat. Our dog ... (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: