1. Natalie

Lots of snuggles and love for your pup!

Near West Side, Chicago, IL, 60607

"I left my little guy, Tito (chihuahua) with Natalie for the first time for an extended time period of almost two weeks. S..."

2. Jessica

Experienced Dog Caregiver (and lover)

Near West Side, Chicago, IL, 60607

"Jessica did an outstanding job. She sent me regular updates with pictures that set my mind at ease. She took Lou out to d..."

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 ..."

4. Bradley

Good time guaranteed

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 goo..."

Confirmed Thanksgiving Availability
5. Lucas

Professionals Offering a Home Away From Home

Lower West Side, Chicago, IL, 60608

"Awesome as always!!! The girls love them some Lucas:)"

6. Jennifer

Dogs Dream Vacation Just A CLICK Away!

Near West Side, Chicago, IL, 60661

"Jennifer has been watching our 4-month old puppy for a couple of months now and we're so happy to have her! She treats eve..."

Confirmed Thanksgiving Availability
7. Grant

Your dog will feel at home!

Loop, Chicago, IL, 60605

"I've known Grant for about 2 years now and ever since the first time I've met him, it is quite apparent he is an animal lo..."

8. Melissa

Furry Paradise

Near North Side, Chicago, IL, 60654

"Excellent dog sitter. I was given updates and pictures during the stay. My dogs were well taken care of and got lots of cu..."

9. 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..."

10. Sarah

Dependable and loving dog care!

West Town, Chicago, IL, 60622

"Sarah was so great with my wheaten terrier. She followed all my instructions and even let Libby sleep with her at night! I..."

11. Janika

Give your dog a sweet vacation too!

Loop, Chicago, IL, 60602

"Nikki was extremely communicative with us throughout Ralphie's stay, always keeping us in the loop with photos and text up..."

12. Valerie

Love, attention, & walks along the lake!

Near South Side, Chicago, IL, 60616

"I am very satisfied with Sumi's stay with Valarie! We were very lucky to have found someone on short notice and we could ..."

13. Amber

Your baby will feel at home, never alone

West Town, Chicago, IL, 60654

14. Deborah

Dog sitter in the loop!

Loop, Chicago, IL, 60607

"Debbie was great keeping us up to date about our dog and making sure he had a happy stay. She paid close attention to him ..."

Confirmed Thanksgiving Availability
15. Yekaterina

Join our Playhouse w/YARD and PARK!

McKinley Park, Chicago, IL, 60609

"Katherine was incredible with my dog Otis! Otis is a LOT of dog to handle - a huge Great Dane and he loved all the attent..."

16. 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-u..."

17. 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 accommoda..."

18. Robert

Your dog may not want to go home!

South Lawndale, Chicago, IL, 60608

"Everything was great Robert and his Wife met with me before the stay went over everything and everything went smooth with ..."

19. 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..."

20. 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 up..."

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