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1. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

3 repeat clients

"Betsey was fantastic. Max was happy and worn out we he got home after a week with her. I would definitely recommend her (more)"

2. Jessica

Your Dog Will Have Fun and Comfort!

Lincoln Park, Chicago, IL, 60614

Dog Boarding

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. 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. Tim

Disciplined and flexible.

West Town, Chicago, IL, 60647

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

7 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)"

5. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

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

3 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)"

6. Alexandra

Crazy Dog Lady

West Town, Chicago, IL, 60612

Dog Boarding

2 repeat clients

"I could not be more relaxed and happy during my holidays! I knew how good my boys were with Alexandra so I really enjoyed my time out of the city! Thank you! (more)"

Available this weekend
7. Gina

Looking for a furry friend!

Near North Side, Chicago, IL, 60610

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

4 repeat clients

"Gina is great! My sometimes "high maintenance" pup was happy and healthy when I returned. I am afraid he is a little bored now with only me to play with. I ... (more)"

8. Ashli

Responsible & Experienced Dog Care!

West Town, Chicago, IL, 60642

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

3 repeat clients

"Ashli took great care of Ella! She was clear and communicative before and during the stay and sent great photo updates that showed that Ella's vacation was a... (more)"

9. Alyssa

Flexible, Active Dog Lovers!

West Town, Chicago, IL, 60642

Dog Boarding

9 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)"

10. Rob

Super caring and work from home

West Town, Chicago, IL, 60622

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

"Rob looked after my Shih Tzu for years when he lived in Boston. He is very patient and gentle as well as reliable about showing up on time, etc. Frisco was a... (more)"

Confirmed Labor Day Availability
11. Bri

Bri's Pooch Palace

Near West Side, Chicago, IL, 60661

Dog Boarding

2 repeat clients

"Bri and Josh were great with my dog Como, who was well cared for upon my return. They also went out of their way to make things convenient for me. Definitely... (more)"

Available this weekend
12. Lyss

Dogs are just really hairy kids.

Near West Side, Chicago, IL, 60612

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

"I would personally recommend Alyssa for watching over your pet dog because of the simple fact that she is responsible. She has a big heart and willing spirit... (more)"

13. Sue

The biggest dog lover in Chicago

Near West Side, Chicago, IL, 60607

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

7 repeat clients

"She was easy to work with and seemed to really enjoy dog sitting. I would use her again in the future. (more)"

14. Caleb

West Loop Dog Lovers

Near West Side, Chicago, IL, 60661

Dog Boarding, Doggy Day Care

"Caleb and Ashley took really good care of Crosby on an overnight stay. With him being a puppy, he needed a little extra attention and they were up to the tas... (more)"

Confirmed Labor Day Availability
15. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was a great sitter and Leena loved her. Mindy is very knowledgeable of dogs and she was able to provide us valuable information about the pitbull breed... (more)"

Available this weekend
16. Vanessa

Fun caring dog lover.

Near North Side, Chicago, IL, 60654

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

4 repeat clients

"Vanessa was great! She sent updates and pics of my puppy Harvey frequently and kept me updated often. Harvey also had her dog to play with and keep him compa... (more)"

17. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

9 repeat clients

"Lor'Enyah was so sweet with my slightly anxious beagle and she was very flexible with scheduling. I will not hesitate to reach out to her again when I am goi... (more)"

18. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

10 repeat clients

"I HIGHLY recommend Bradley to sit for your best buddy! He was incredibly attentive to my Bichonpoo THOR. His dogs Bolt&Apollo are very sweet and gentle. I wi... (more)"

19. 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)"

Confirmed Labor Day Availability
20. 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)"

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Dog Boarding in Chicago

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

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: