Dog Boarding in Washington Park, Chicago

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

1. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

28 repeat clients

"My husband and I went to Mexico for a week and our maltipoo Sammy stayed with Jessica and her boyfriend David for 9 nights! This is the longest we have ever ... (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. 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)"

4. 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)"

5. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Magdalena was truly a wonderful pet-sitter. From sending us daily pics and updates, to being almost angelically accommodating when our flight was delayed to ... (more)"

6. 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)"

7. 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)"

8. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"Elesha was great with my Bella, she had a great time! I got many wonderful updates during her stay. She took Bella on many walks and gave her lots of love. I... (more)"

9. 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)

10. 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)

Confirmed Thanksgiving Availability
11. Samantha

Weekend doggy oasis

Gage Park, Chicago , IL, 60632

Dog Boarding, House Sitting

"Samantha was great! She's very patient. I've been trying to find Chloe a dog sitter who can deal with her personality for a long time and I've finally found ... (more)"

12. 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)"

13. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"LeAnna has a passion for animals of all kinds, but she really shines with dogs - I don't think I've ever seen a dog that didn't like her almost instantaneous... (more)"

14. 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)"

15. 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)"

16. 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
17. 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)"

18. 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)"

19. Shellie

Love dogs, owned them for years

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care

"My Pooch was so spoiled during his stay with Shellie...he was so well-taken care of. He's a fiery minpin so I was a little nervous about how he would be wit... (more)"

20. Randi

Loved animals all my life.

West Englewood, Chicago, IL, 60636

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

About: Hi everyone my name is Randi I am a 22 year old college student and I enjoy animals especially dogs and cats. I think its because they show you how... (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: