1. Frank

Baby It's Cold Outside.

Lower West Side, Chicago, IL, 60608

"Frank is a nice, generous, and understanding person but more importantly he is a spectacular dog sitter. I visited Max during his stay and I could tell how m... (more)"

2. 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)"

3. 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 dinner, on car rides and walks. He ... (more)"

4. Anne

Dog sitting, daycare or walking!

West Town, Chicago, IL, 60642

"Charlie had a great stay with Anne and Gertie! Anne was super friendly made it easy to coordinate drop off and pick up. I'll definitely go to Anne again when... (more)"

5. Nick

I'm a dog person.

Loop, Chicago, IL, 60607

"Nick watched my dog pancake while i was on vacation and he sent me pictures of her almost every day! She had a great time with nick. (more)"

6. 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)"

Confirmed Easter Weekend Availability
7. Risa

Stay at home puppy mom - Dawg House

Near West Side, Chicago, IL, 60607

"Risa and Matt are a very responsible young couple and dedicated dog owners They love dogs, and make their young poodle's health and training a priority. (more)"

Confirmed Easter Weekend Availability
8. 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)"

Confirmed Easter Weekend Availability
9. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

"Great sitter! Magdalena was very responsive, timely, sent cute pics, and flexible with my schedule. I would definitely recommend her for your pooch! (more)"

10. 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)"

Confirmed Easter Weekend Availability
11. Jennifer

Doggie B&B

Lower West Side, Chicago, IL, 60608

About: Hello Rover pet owners. My Name is Jenny, I am an absolute dog lover of all breeds and sizes, I've had dogs all throughout my life growing up and j... (more)

12. 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)"

13. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

"I HIGHLY recommend Bradley to sit for your best buddy! He was incredibly attentive to my Bichonpoo THOR. His dogs Bolt&Apollo are very sweet and gentle. I wi... (more)"

14. Jenna

Fun for your four-legged friend!

Near West Side, Chicago, IL, 60608

"Jenna was so great! Fairley came home so tired and happy. I loved all the pictures she sent and also a video of Fairley and Ellie May playing which was wonde... (more)"

15. 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)"

16. 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)"

Confirmed Easter Weekend Availability
17. 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)"

18. Megan

Your dog will be part of our family.

Near West Side, Chicago, IL, 60607

"Megan was a great sitter for our little one. He came up exhausted and we received pictures throughout his stay. Thank you so, so much! (more)"

19. Robert

Your dog may not want to go home!

Lower West Side, 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)"

20. 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)"

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