1. Holly

Poodle Mommy for sitting/walking!

Lower West Side, Chicago, IL, 60608

"Holly was extremely attentive to Solomon's needs. She made sure to accommodate us and provided such an excellent service. Her sitting surpassed our wildest i... (more)"

2. Risa

Stay at home puppy mom - Dawg House

Near West Side, Chicago, IL, 60607

"Risa was great with my puppy DuDu! She treated DuDu as if she's her own, very caring and loving. The best thing is that my puppy had such a fun time playing ... (more)"

3. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

"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)"

4. Frances


Near North Side, Chicago, IL, 60654

"Frances took great care of my dog Bear! She sent pictures everyday, and even took him out for long runs and fixed his broken harness. Her love for animals ... (more)"

Available this weekend
5. Kristina

a favorite aunt to you pet

Bridgeport, Chicago, IL, 60608

About: I am a lover of all animals and they end up loving me back. I am working at a dog hotel and daycare during the day from 6am-2pm. and have had anima... (more)

Available this weekend
6. Jennifer

Doggie B&B

Lower West Side, Chicago, IL, 60608

"Absolutely LOVED having Charlie stay with Jennifer, she kept kept me updated with him and also sent me pictures. She is super sweet as well, I would def have... (more)"

7. April

Dog Walking/Sitting in South Loop!

Near South Side, Chicago, IL, 60605

"No words can express how appreciative I am of April. She is a stellar dog-sitter and has become a friend. Her dog Nala is exceptionally well behaved and is a... (more)"

8. Frank

Baby It's Cold Outside.

Lower West Side, Chicago, IL, 60608

"Frank is such a kind and accommodating dog sitter. He has a dog friendly set up and my dogs really enjoyed their stay. I feel really good knowing my dog's ha... (more)"

9. Allison

A vacation for your pup!

West Town, Chicago, IL, 60642

"Couldn't have picked a better sitter for my first time. (more)"

10. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

"Madga was fantastic with Jethro. She sent me daily updates and was very easy to work with regarding drop off and pick up. I totally recommend her! Jethro cam... (more)"

11. Megan

Gracie would love to share her toys.

Near West Side, Chicago, IL, 60607

"Loved having Charlie stay at Megan's! Charlie got along great with her dog Gracie, she even set up a meetup before so we can see how our pups would get along... (more)"

12. M Patrick

Dog Lovers For Weekend Sitting

Loop, Chicago, IL, 60605

"Amanda and Mike were fantastic sitters for Quinn. A few days before needing a sitter, I found myself in a bind and searched Rover. Mike responded right away ... (more)"

13. Jessica

Experienced Dog Caregiver (and lover)

Near West Side, Chicago, IL, 60607

"Jessica is awesome! Having had a prior bad experience with boarding my "baby" Caleb, I was extremely cautious and skeptical about using this service. Jess... (more)"

14. Megan

Medical student/Dog lover

Near North Side, Chicago, IL, 60611

"Megan is wonderful! She took Butternut on short notice and gave her lots of love and affection. I received updates and photos throughout the days and Buttern... (more)"

15. Hilda

Family environment - Your dog will feel at home!

Brighton Park, Chicago, IL, 60632

"Hilda was very attentive at our meet and greet. She asked plenty of questions. During the stay she sent lots of photos and updates. We have already booked he... (more)"

16. Nick

I'm a dog person.

Loop, Chicago, IL, 60607

"Nick was excellent. He bathed Dutch without us asking and took him on long walks. I was incredibly happy with Nick and tipped him because he did such a grea... (more)"

17. Richa

Loving couple who love pets!!

Near South Side, Chicago, IL, 60605

About: My husband and I are home most of the time with our puppy if we are not at the dog park. Our little pup loves to play and would love to have a slum... (more)

18. Esther

Lovely Dog Sitter in the Prairie District

Near South Side, Chicago , IL, 60616

"Esther watched my dog this past weekend and it was a great experience, it was my first time using a sitter and i was very happy with it. From th... (more)"

19. Brooke

Doggie haven in West Town.

West Town, Chicago, IL, 60622

"I highly recommend Brooke for you dog watching needs. She responded quickly to all inquiries and was very flexible with her dropoff/pickoff availability. ... (more)"

20. Anne

Dog sitting, daycare or walking!

West Town, Chicago, IL, 60642

"This was our first experience using Rover, so we were a bit nervous to begin with. Anne was great! She easily arranged a meet and greet so we could make sure... (more)"

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Dog Boarding In Chicago

The Chicago Dog Kennel Alternative

Dog owners love Rover's Chicago dog sitters. 1,724 owners have reviewed sitters in Chicago, giving them an average rating of 5/5.

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. - Dog Boarding Community