1. Frank

Baby It's Cold Outside.

Lower West Side, Chicago, IL, 60608

"Frank did an awesome job with our dog Napolean! He communicated everyday through updates and wonderful pictures. He was very friendly and professional. T... (more)"

Available this weekend
2. Sofia

Home away from home

Near North Side, Chicago, IL, 60654

"Wonderful! (more)"

Available this weekend
3. Risa

Stay at home puppy mom - Dawg House

Near West Side, Chicago, IL, 60607

"Risa was great!! She was super responsive and gave me daily updates + pics on how Moose was doing! I really appreciate how Risa scheduled time before hand to... (more)"

Confirmed Memorial Day Availability
4. 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)"

5. Frances


Near North Side, Chicago, IL, 60654

"Frances was great !! She would keep us updated about my dogs stay all the time ! I received pictures of my dog all the time and she seemed to be having a gre... (more)"

6. 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)"

7. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

"Lor'Enyah was great at giving me multiple updates on Lilly throughout her stay. She comes highly recommended. (more)"

8. Jennifer

Doggie B&B

Lower West Side, Chicago, IL, 60608

"Excellent sitter! Jennifer kept me updated regularly with pictures and messages. Johnny Boy was happy when I dropped him off and picked him up he was very co... (more)"

9. 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)"

Available this weekend
10. Jessica

Experienced Dog Caregiver (and lover)

Near West Side, Chicago, IL, 60607

"My husband and I went to Mexico for a week and our maltipoo Sammy stayed with Jessica and her boyfriend David for 9 nights! This is the longest we have ever ... (more)"

11. Brooke

Doggie haven in West Town.

West Town, Chicago, IL, 60622

"Brooke was great and very accommodating. Although we had a couple of glitches in our travel plans, communication was easy and stress-free. Brooke also sent r... (more)"

12. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

"Bradley was awesome! He took very good care of Soni. She was sad to leave him which was a first we have seen from her outside of family. He kept us updated o... (more)"

13. 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)"

Confirmed Memorial Day Availability
14. Dana

At home sitter.

Lower West Side, Chicago , IL, 60608

About: I have caregiving experience. I was a caregiver for 6 years. I would cook, clean, help in the bathroom, companionship, and help administer meds. ... (more)

Confirmed Memorial Day Availability
15. Nina

Nina's dog camp

New City, Chicago, IL, 60609

"My little Koko and Kahj had such a fabulous stay at Nina's! It was their own little retreat, a home away home! Ok, so where do I begin?!? I had to find some... (more)"

16. Lauren

Bring 'em on over!

Grand Boulevard, Chicago, IL, 60653

"We couldn't have found a better dog-sitter for our dog, Duke. Lauren was excellent. We had great communication with her from the time we were exploring possi... (more)"

17. Leah

Single girl wants company

Near North Side, Chicago, IL, 60611

"Leah is absolutely fantastic. She professional, timely, reliable....most importantly, she treated my pup like her own! Maddie (my pup) had a great time durin... (more)"

18. 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)"

19. Ashley

Inner City Dog Sitting.

Loop, Chicago, IL, 60601

"Ashley was so wonderful!!! She sent pics everyday & I could tell that Vixen was having a great time. Ashley is very knowledgeable about dogs and I'm pretty ... (more)"

20. Amber

Your baby will feel at home, never alone.

West Town, Chicago, IL, 60654

"Amber took care of my puppy Bear, a mini goldendoddle, for an entire week over the holidays! She was great and sent us pictures throughout his stay. It was ... (more)"

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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