To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
1. Jessica

Experienced Dog Caregiver (and lover)

Near West Side, Chicago, IL, 60607

"I have to say, Jessica did a great job of taking care of Java. Java's a rescue and is very timid in new surroundings, but she was very patient and caring. ... (more)"

2. Natalie

Lots of snuggles and love for your pup!

Near West Side, Chicago, IL, 60607

"Natalie took such good care of Frankie. Lots of pictures and communication along the way. And she even noticed his small rash which I'd forgotten ointment f... (more)"

3. Hilda

Family environment - Your dog will feel at home!

Brighton Park, Chicago, IL, 60632

"My dog Deacon had a great time with Hilda this past weekend. He is a larger dog, but enough used to apartment living that I knew a small space would work for... (more)"

4. Grant

Your dog will feel at home!

Loop, Chicago, IL, 60605

"Grant was excellent with watching our two pups last weekend while we were out of town. It was our first experience using Rover and we were very pleased. He w... (more)"

Available this weekend
5. Jaclynne

Downtown Lady will Love Your Pooch!

Loop, Chicago, IL, 60606

"I travel quite a bit for work, and have been looking for a nice place for Mikey to stay while I am away. I think the search is over. :) First of all, Jaclynn... (more)"

6. Bradley

Good times to be had

Near West Side, Chicago, IL, 60608

"Bradley was able to take in Harley last minute for an overnight stay and was extremely accommodating. He guaranteed a good time and Harley was not disappoin... (more)"

7. Lauren

Bring 'em on over!

Grand Boulevard, Chicago, IL, 60653

"Lauren is a phenomenal caregiver to my little one, Musik. I can always count on her to provide the utmost care for her. Walks in the park, playtime,and even... (more)"

Confirmed Holiday Availability
8. Jonathan

Experianced dog sitter

Lower West Side, Chicago, IL, 60608

"Johnathan has a love for animals that, a lot of times surpasses his love for humans. Since I can remember Jonathan has always been passionate and nurturing t... (more)"

Confirmed Christmas Availability
9. Aryn

We welcome your dog into our home!

Near North Side, Chicago, IL, 60611

"I couldn't have picked a better pet sitter for Barney. She kept me updated throughout the entire stay and would send me pics daily! I'd reccomend Aryn to an... (more)"

10. Andrey

very friendly and reliable , dog owner

Loop, Chicago, IL, 60601

"Andrey is great. He was able to take my dog on very short notice and was extremely accommodating. He sent updates and pics throughout the stay and was very r... (more)"

11. Janika

Give your dog a sweet vacation too!

Loop, Chicago, IL, 60602

"Coby stayed with Janika for about a week and loved it. (more)"

Available this weekend
12. Valerie

Love, attention, & walks along the lake!

Near South Side, Chicago, IL, 60616

"Valerie was wonderful with Bear! She took time to send daily updates with pictures and took great care of Bear! He came home pooped :) I would highly recomm... (more)"

13. Andrea

Keeping your dog busy while you're gone!

Near North Side, Chicago, IL, 60611

"Andrea was awesome! She was super flexible with pickup and drop off times and very accommodating. Andrea sent picture updates throughout the weekend and I ... (more)"

14. Colleen

We love making furry friends!

Lower West Side, Chicago, IL, 60608

"Colleen was great! I felt so much better about leaving Ash with a person with my same schedule than a kennel where he'd be crated most of the day. Colleen wa... (more)"

Confirmed Holiday Availability
15. Robert

Your dog may not want to go home!

South Lawndale, Chicago, IL, 60608

"As always, Maddie had a great stay here. This was the second time using Robert and his wife and Maddie ran right up the stairs when we dropped her off. Tha... (more)"

16. Lauren

Home Away Home

Near West Side, Chicago, IL, 60607

"Cici only stayed for one night, but she seemed happy and well taken care of when I picked her up. Kati was very accommodating with my crazy work schedule an... (more)"

17. Mike

Your dog will get as much love as my dog.

Near West Side, Chicago, IL, 60607

"Mike was a great and reliable sitter, very easy... Would trust my dog with him again -has a front yard and is highly recommended. Thx mike! (more)"

18. Lesley

Lots of love and attention!

Loop, Chicago, IL, 60601

"This was the first time away from home for my two little Chihuahuas. Lesley was very patient with barking through the night , pees on the rug, and overall lo... (more)"

19. Rebecca

Loving Care in the Heart of Downtown!

Loop, Chicago, IL, 60601

"I've known Becca for years, and she has always been great with my dogs. She's always willing to do any unpleasant clean-up without complaint. My dog loves ... (more)"

20. Sarah

Smart and active sitter

West Town, Chicago, IL, 60642

"The hardest thing for me to do is to leave my dog. Sarah is a very knowledgeable and trusting provider.I have no worries at all with my dog in her care. She ... (more)"

Dog Boarding In Chicago

The Chicago Dog Kennel Alternative

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