Dog Boarding in Oakland, 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

"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)"

2. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

"Megan is a true dog lover. Her pooch, Duffy, is a happy, healthy, loving, and well-loved canine. She has great instincts and has trained him well! (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

"Sara would give excellent care to any animal. Beginning at a young age, Sara has had pet dogs. She has given loving care for each animal that was in our home... (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)"

Confirmed Thanksgiving Availability
7. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Magdalena was amazing!! She sent several pictures of my baby during his stay, was able to get him to eat when most others can't, and was incredibly flexible ... (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. 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)

10. 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)

11. 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)"

12. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

"Martin watched my 2 large, rambunctious Hound dogs for about a week. He was very friendly, easy to work with, and great with the dogs! I would 110% recommend... (more)"

13. 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)"

14. Anquin

Young Dog Friendly Professional

Hyde Park, Chicago, IL, 60637

Dog Boarding

About: I have had dogs all throughout my childhood, and would most often be the go to person for dog sitting among friends and family members growing up! ... (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

"Danielle was very accommodating! My flight left very, very early and returned very, very late. My dog, Tessa, seemed to enjoy her stay. Would definitely ... (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. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"My family and I were visiting Portland and needed a day off to explore indoor areas sans our little buddy. Our dog was very happy to spend the day with Elesh... (more)"

19. Hika

Your Dog will be Loved by our Family!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"Hika is a fantastic sitter and really loves dogs. When I first met her I could feel her gentle spirit and my dog Bruce had no intimidation. When she took his... (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)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: