1. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

2 repeat clients

"Betsey is amazing!!! Sasha had a great time. (more)"

2. Jessica

Your Dog Will Have Fun and Comfort!

Lincoln Park, Chicago, IL, 60614

2 repeat clients

"Jessica was really great with my dog. She was flexible and extremely friendly. She sent me a picture of my dog during his stay, and he seemed very content.... (more)"

3. Christine B. & Jessica

Dogs>Humans-Roommates who Love Pups

Near South Side, chicago, IL, 60605

4 repeat clients

"This was Gracie's first Rover home stay and I have to say Christine and Jessica were great! They were very flexible with our schedule and most importantly G... (more)"

4. Waverly

Soon to be Dr.Wave!

Grand Boulevard, Chicago, IL, 60653

9 repeat clients

"I swear, my dog didn't even want to come home. Waverly was the perfect sitter; even when travel got in the way, she was 100% accommodating. She has a huge fe... (more)"

Available this weekend
5. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

3 repeat clients

"Lauren was fantastic. She provided me daily updates and pictures and was super easy to work with. She was very accommodating. I plan on asking for her help ... (more)"

6. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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)"

7. Tim

Disciplined and flexible.

West Town, Chicago, IL, 60647

5 repeat clients

"Tim was wondering with gizmo, i was updated with the daily adventures and given lots of photos. When i picked up gizmo he was seemed so relaxed and happy to ... (more)"

8. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

3 repeat clients

"Brittany was awesome. Napoleon's stay was the first with her and she was so nice and thoughtful--sent me pictures. Communication was great before and after p... (more)"

Available this weekend
9. Alice

Your dog will have fun with me!

Near North Side, Chicago, IL, 60611

"I have left my Pomeranian, Bella, with Alice and Elliott before. Bella loved them both! Alice was able to provide multiple walks around the neighborhood and ... (more)"

10. Nousha

Dogs are People, too!

Near North Side, Chicago, IL, 60611

"Nousha is great with dogs and I'd trust her with mine any day. I myself am an animal lover and experienced Rover employee and i have full confidence in Noush... (more)"

11. Ashli

Responsible & Experienced Dog Care!

West Town, Chicago, IL, 60642

1 repeat client

"We never worried once while Ashley had our babies! We could tell upon meeting her she loves dogs and that's why she doggie sits. She was very easy to communi... (more)"

12. Sarah

Dog Loving Friendly Lady

Near West Side, Chicago, IL, 60612

3 repeat clients

"Sarah was very professional and thoughtful to my dog. Her place has a very good environment for dog boarding. She send pictures frequently to let me know my ... (more)"

13. Wen Tze

Experienced and reliable pup lover!

Bridgeport, Chicago, IL, 60609

About: I love any and all types of dogs! They're my furbaby and if you're an absolute pup lover like me, you'll understand how much more I would care for ... (more)

14. Alejandra

Loving Care When You're Not There

Near West Side, Chicago, IL, 60607

"Alejandra is a great sitter! We had to leave town unexpectedly and she was able to accommodate us on short notice. She kept us informed about Ella's stay and... (more)"

15. Bri

Bri's Pooch Palace

Near West Side, Chicago, IL, 60661

2 repeat clients

"Bri is a huge dog-lover! She grew up with dogs at home so she knows what it takes to keep them safe & happy. She is a natural caregiver who always looks out ... (more)"

16. Sue

The biggest dog lover in Chicago

Near West Side, Chicago, IL, 60607

4 repeat clients

"Sue is a huge dog lover! She has a lot of experience as a foster mom to homeless dogs. This involves bringing them into her home, caring for them while with ... (more)"

17. Caleb

West Loop Dog Lovers

Near West Side, Chicago, IL, 60661

"Caleb and Ashley took great care of Lucy! She lived a weekend of luxury in the Windy City. We're so grateful for how well they took care of our girl. ? (more)"

18. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

10 repeat clients

"This is the second time Charlie has stayed with Bradley and everything went great. Extended stays are always challenging but Charlie loves hanging with the ... (more)"

19. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

2 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)"

20. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

8 repeat clients

"I am not sure "how" Lor'Enyah G. was able to get my monster act right. But we are very happy and look forward to leaving home again and using her again. T... (more)"

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Dog Boarding In Chicago

The Dog Kennel Alternative

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: