Available this weekend
1. Rachel

~Pet-Pampering Oasis~

Lincoln Park, Chicago, IL, 60614

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"Rachel was absolutely amazing with Winston. He has anxiety and Rachel took great care of him. She sent lots of pictures throughout the weekend and I could ... (more)"

2. Corina

Running & Loving fur Paws!

Lake View, Chicago, IL, 60657

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

4 repeat clients

"Corina was extremely responsive throughout our dog's stay, and provided our dog with a great mix of exercise and relaxation. Would highly recommend if you ar... (more)"

3. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

3 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)"

4. 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)"

5. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"She is fantastic with my dog! (more)"

6. Meegan

Trustworthy recent college graduate

Loop, Chicago, IL, 60605

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

"Meegan was wonderful to deal with. She kept in touch with updates and Bugsy seemed to have a great time at her place could definitely recommend! (more)"

7. 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)"

8. Alyssa

Flexible, Active Dog Lovers!

West Town, Chicago, IL, 60642

Dog Boarding

10 repeat clients

"We cannot say enough great things about Alyssa! From meet-and-greet to drop off, sending picture updates and videos to pick-up, Alyssa was even more perfect ... (more)"

9. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

10 repeat clients

"Lor'Enyah was great! She was very accommodating, flexible, and knowledgeable. Whenever I need someone to watch my dog again, I will definitely reach out to h... (more)"

10. 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)"

11. Kezia 'vivani'

Pilsen dog lover :)

Lower West Side, CHICAGO, IL, 60608

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: Hello everyone, my name is Kezia :) I manage the scheduling department for a home health agency but secretly I wish I were a stay at home mom to 2 ... (more)

12. 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)

13. Andrew

A Dog-Loving Law Student

Loop, Chicago, IL, 60604

Dog Boarding, Drop-In Visits, Dog Walking

4 repeat clients

"Andrew did a great job with Cody while I was on an international trip. Before the trip he was extremely responsive in any questions I had and making sure a ... (more)"

14. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"Lauren and her dog welcomed my dog lovingly into their home. He played in the park and enjoyed himself thoroughly. She sent pictures of their adventures to... (more)"

15. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

11 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)"

16. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

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

4 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)"

17. 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)"

18. Claire

Dog-lover downtown!

Loop, Chicago, IL, 60607

Dog Boarding

"Claire was super easy to work with, sent pics, and took such good care of Frankie while I was away. (more)"

19. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Magdalena is great! Always my first pick. She is wonderful with our shy girl, who takes awhile to warm up to people. Ellie always comes back happy and exhaus... (more)"

20. Jessica

West Town Dog Lover!

Near West Side, Chicago, IL, 60642

Dog Boarding

2 repeat clients

"Great experience!! Arpels had a great time at Jessica's place. She took him for long run every morning, and to beach on the weekend. Definitely come back to ... (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: