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1. Kristina

A favorite aunt to your loved one

Bridgeport, Chicago, IL, 60608

14 repeat clients
14 reviews

"Super love Kristina! I needed someone on Thanksgiving but some Rover sitters were being flakey, unavailable or just didn't fit my criteria. My dog gets sad ... (more)"

2. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

28 repeat clients
88 reviews

"As always, Digby seemed to have an excellent time. :) Thanks for being such a great sitter and providing us with yet more cute pics of our dog! (more)"

3. Lu

Dog loving couple in Streeterville!

Near North Side, Chicago, IL, 60611

8 repeat clients
19 reviews

"Lu was fantastic! She sent a ton of great photos and updates, was easy to work with and schedule, and extremely responsive. I can tell my dog had a great tim... (more)"

4. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

1 repeat client
3 reviews

"Samantha was great to work with, and her own dog, Waffles, is very cute and friendly. Samantha took careful notes about our pup's schedule, habits, and medic... (more)"

5. Emily

City-Slicking Dog Lover

Near West Side, chicago, IL, 60607

About: My existence has been surrounded by dogs. In my 22 years of life I have had 3 dogs and l loved them all dearly. My current canine child's name is b... (more)

6. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

1 repeat client
2 reviews

About: Chad and I have had dog companions our entire lives. Together we have cared for these loved ones for over 40 years combined. We treat guests as m... (more)

7. Christine B. & Jessica

Dogs>Humans-Roommates who Love Pups

Near South Side, chicago, IL, 60605

2 repeat clients
7 reviews

"This was by far the best and first experience I have had with Rover. Not only was Jessica and Christine extremely professional but they were also very genuin... (more)"

8. Vanessa

Fun caring dog lover.

Near North Side, Chicago, IL, 60654

"Vanessa was great! She kept me updated with texts and photos of my little guy while I was away and he seemed super happy when I went to pick him up. I would ... (more)"

9. Bri

Bri's Pooch Palace

Near West Side, Chicago, IL, 60661

1 repeat client
3 reviews

"Bri is wonderful with animals. She has experience with all sizes of dogs. She is friendly and dogs take to her well. She can sit for my dogs anytime. Very re... (more)"

10. Andrew

A Dog-Loving Law Student

Loop, Chicago, IL, 60604

"I have known andrew for over 3 years now and he is one of the most responsible and organized people I know. He takes amazing care of his corgi, Pork Chop, go... (more)"

11. Marissa

Friends Needed for Quinn

Loop, Chicago, IL, 60607

About: My fiance and I have had dogs our entire lives, and even have a special little guy in our life right now named Quinn. We make sure he has the best ... (more)

12. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

9 repeat clients
28 reviews

"We're about to take our first trip away from our puppy Duncan and were nervous about finding him a place to stay while we're gone. We left him with Bradley ... (more)"

13. Elizabeth

Ivy League Dog Lover

Loop, Chicago, IL, 60604

1 repeat client
9 reviews

"Elizabeth was great with Teddy! She is very responsible and responds quickly to texts. I appreciated the daily pictures and updates, and felt at ease while... (more)"

Confirmed Memorial Day Availability
14. Caitlin

trustworthy & friendly pup lover!

Near West Side, Chicago, IL, 60661

"Caitlin was a great sitter for our little Lola. We had a last minute need for a sitter and she was very accommodating and excited to have her for the weeken... (more)"

15. Heather

Needs more dog friends.

Loop, Chicago, IL, 60604

"Amazing!first time using Could not have been a better experience. Will definitely use Heather again if we are in the Chicago area. And will use Ro... (more)"

Confirmed Memorial Day Availability
16. Jane

Don't want no scrubs - puppies only

West Town, Chicago, IL, 60642

"Jane was awesome. Very responsive, sent lots of updates and pictures. Our 5 year old chow mix Barksdale had a great time and he even got to go on a hiking t... (more)"

17. M Patrick

Dog Lovers For Weekend Sitting

Loop, Chicago, IL, 60605

2 repeat clients
7 reviews

"Amanda and Mike were fantastic sitters for Quinn. A few days before needing a sitter, I found myself in a bind and searched Rover. Mike responded right away ... (more)"

18. Jenna

Fun for your four-legged friend!

Near West Side, Chicago, IL, 60608

11 repeat clients
15 reviews

"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)"

19. Bryce

Passionate & Responsible Care Giver

Lower West Side, Chicago, IL, 60608

2 repeat clients
7 reviews

"Bryce tired out my high-energy dog, replied to all my messages promptly, and was gracious and accommodating when my return trip was delayed by a couple hours... (more)"

Confirmed Memorial Day Availability
20. Ida

A home away from home

Bridgeport, Chicago, IL, 60609

1 repeat client
3 reviews

"Ida was a great match for taking care of our Harlowe. She is friendly, professional, caring and great at communication. She was awesome at texting photos t... (more)"

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Dog Boarding In Chicago

The Dog Kennel Alternative

Dog owners love Rover's Chicago dog sitters. 1,724 owners have reviewed sitters in Chicago, giving them an average rating of 5/5.

Wondering how much you can expect to pay for a night on Check out our average dog sitting rates to get an idea before you start a conversation with a sitter.

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 nonprofits across the U.S., including:

More on Chicago

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.

Useful Info on Dogs - Dog Boarding Community