36 dog loving sitters matched
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

"I really cannot say enough about how great Jessica was! From the moment I contacted her she was incredibly responsive and ..."

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. 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 ..."

5. Lucas

Professionals Offering a Home Away From Home

Lower West Side, Chicago, IL, 60608

"Amazing sitter!! It was wonderful having Coby stay with Lucas. He updated me frequently about the stay, and he truly went ..."

6. 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..."

7. 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..."

8. 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..."

9. Janika

Give your dog a sweet vacation too!

Loop, Chicago, IL, 60602

"Janika was great. So nice, and sent me photos of my baby every day! My pup loved her. She took him to the park multiple t..."

10. 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..."

11. Valerie

Love, attention, & walks along the lake!

Near South Side, Chicago, IL, 60616

"Very helpful and accommodating. Would definitely recommend. "

12. 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..."

13. Jennifer

Dogs Dream Vacation Just A CLICK Away!

Near West Side, Chicago, IL, 60661

"Jennifer of Poopanators, is known as Auntie Jen at our house. She enhances the quality of our spunky chihuahua's life on a..."

14. 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..."

15. 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 ..."

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 accommoda..."

17. 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 ..."

18. 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..."

19. 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 recom..."

20. 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..."

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