44 dog loving sitters matched
1. Mike

Dog free to roam! I work from home!

Near South Side, Chicago, IL, 60605

"Mike was fantastic! He made sure Hank's routine at his house as as close to his everyday routine at my own, asked lots of..."

2. Jessica

Experienced Dog Caregiver (and lover)

Near West Side, Chicago, IL, 60607

"Jessica helped make our first experience with Rover a great one. Friendly, attentive, and great at communicating, Jessica ..."

3. Baselia

The Lovable Doggy Nanny

Lower West Side, Chicago, IL, 60608

"Baselia was AMAZING! She kept me updated with pictures and when I needed to extend my trip at the last minute Baselia was ..."

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..."

5. Patty

We love new friends! from Pilsen to Lakeview

South Lawndale, Chicago, IL, 60608

"Poki and Peanut stayed with Patty for 9 nights."

6. Hilda

Family environment - Your dog will feel at home!

Brighton Park, Chicago, IL, 60632

"I took my dog Mitt to Hilda's for the day and he had a great time. Hilda loves dogs and her 12 year old dog Baby was a gre..."

7. Kristin

Reliable and loving dog-sitter

Near West Side, Chicago, IL, 60661

"I was really nervous to leave my dog with someone I didn't know, but Kristin made us feel extremely comfortable. She was g..."

8. Lucas

Professionals Offering a Home Away From Home

Lower West Side, Chicago, IL, 60608

"Both Bolt and Apollo have a very fun time with Lucas and he was very accommodating with drop off and pick up times. Th..."

9. Sarah

Dependable and loving dog care!

West Town, Chicago, IL, 60622

"Sarah was very responsive and it made for a great stay for Charlie. "

10. 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..."

11. 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..."

12. Janika

Give your dog a sweet vacation too!

Loop, Chicago, IL, 60602

"Nikki was such an amazing host to Football and Tom Yum!!! Nikki did a great job updating us with picture throughout the da..."

13. Deborah

Dog sitter in the loop!

Loop, Chicago, IL, 60607

"Our dog Muffin had a great stay with Debbie and her little dog Moose. She accepted our reservation at the very last minut..."

14. Jennifer

Dogs Dream Vacation Just A CLICK Away!

Near West Side, Chicago, IL, 60661

"Jennifer has been watching my little Lhasa Aspso princess for around 7 months now and I couldn't be happier with her. I'm..."

15. 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..."

16. Valerie

Love, attention, & walks along the lake!

Near South Side, Chicago, IL, 60616

"The dogs were exhausted after their weekend with Valerie. They loved their stay, thanks again!"

17. Robert

Your dog may not want to go home!

South Lawndale, Chicago, IL, 60608

"Lady spent a long weekend with Robert and had a great time! We got frequent updates and super adorable pictures of Lady wi..."

18. Colleen

We love making furry friends!

Lower West Side, Chicago, IL, 60608

"Colleen and Steve would be great Dog sitters for anyone! Both animal lovers, compassionate, and very responsible. Their ..."

19. Lesley

Lots of love and attention!

Loop, Chicago, IL, 60601

"Lesley was awesome! She kept me posted on everything that was going on with Riley. I really appreciated her!!! Thanks agai..."

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, IL

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