1. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

26 repeat clients
88 reviews

"Our dog Gustav recently stayed 4 nights with Jessica and David. We could tell how much they love dogs during the first meet and greet, and they asked all the... (more)"

2. Lu

Dog loving couple in Streeterville!

Near North Side, Chicago, IL, 60611

5 repeat clients
15 reviews

"The best sitters we have used. They are absolutely wonderful with excellent communication skills. I could tell that my dog was loved and cared for. They send... (more)"

Confirmed Memorial Day Availability
3. Alyssa

Flexible, Work-at-Home Dog Lovers!

West Town, Chicago, IL, 60642

2 repeat clients
12 reviews

"Alyssa was awesome. If dogs could talk I am certain that Ruby's review would be so much better than what I can possibly say. Alyssa sent daily updates with p... (more)"

4. Bri

Bri's Pooch Palace

Near West Side, Chicago, IL, 60661

1 repeat client
3 reviews

"Bri is a huge dog-lover! She grew up with dogs at home so she knows what it takes to keep them safe & happy. She is a natural caregiver who always looks out ... (more)"

Confirmed Memorial Day Availability
5. 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)"

6. Mia

Pawsome B&B on River WalK

Loop, chicago, IL, 60601

5 repeat clients
5 reviews

"Mia was awesome and Cassie was well taken care of. She provided regular updates and was able to work with me, when my flight was a little late. (more)"

7. Christine B. & Jessica

Dogs>Humans-Roommates who Love Pups

Near South Side, chicago, IL, 60605

"the girls were great! super friendly and someone was with Herbie all the time. He got tons of attention, and i got daily updates. they accommodated my specia... (more)"

8. Elizabeth

Ivy League Dog Lover

Loop, Chicago, IL, 60604

1 repeat client
9 reviews

"Lizzie kept me updated about how Napoleon was doing throughout his stay. When we left he was a bit sad to go and a little tuckered out from his adventures. D... (more)"

Confirmed Memorial Day Availability
9. Robb

Probably a dog in a past life :-)

Near South Side, Chicago, IL, 60616

"Robb probably loves dogs more than anything else, and dogs love him back! He's extremely responsible and attentive with his own dog, Scooby, who requires a l... (more)"

10. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

1 repeat client
2 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)"

11. Karina

Play dates anyone?

West Town, Chicago, IL, 60622

1 repeat client
3 reviews

"Karina was great at taking care of Milo. We got tons of adorable pictures, and she was always quick to respond when we had questions. We would love to have h... (more)"

Confirmed Memorial Day Availability
12. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

6 repeat clients
20 reviews

"Chloe had a wonderful stay with Lor'enyah She kept me updated with messages and pictures. I'd recommend her and wouldn't hesitate booking another stay! (more)"

Confirmed Memorial Day Availability
13. Jane

Don't want no scrubs - puppies only

West Town, Chicago, IL, 60642

"Jane was great with our 4.5 month puppy. She sent us pictures and updates of how Hazel was doing and was flexible with our schedule. We will definitely book ... (more)"

14. Marina

An English couple & their Schnauzer

Loop, Chicago, IL, 60601

1 repeat client
3 reviews

"Marina did an amazing job taking care of our pup. She kept us updated throughout his stay at all times. We are very thankful. (more)"

15. Rohit

Reliable & Responsible

Near West Side, Chicago, IL, 60661

4 repeat clients
12 reviews

"Rohit did a great job. He took Rocky and Rico for an evening on short notice. My wife said that when she dropped them off they did not even look back at her ... (more)"

16. Katie

Two humans and a beagle

Near South Side, Chicago, IL, 60605

"Katie was awesome and sent us pictures of our dog throughout her entire stay! She was very flexible with pickup and drop off times and we could tell that sh... (more)"

Confirmed Memorial Day Availability
17. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

9 repeat clients
26 reviews

"Bradley did a great job with Jimmy during the visit. Jimmy came back totally exhausted from having so much fun at the dog park, and was in great spirits all ... (more)"

18. Brett

Chloe loves all playmates!

Near North Side, Chicago, IL, 60611

"I feel like we won the Dog Daycare Lottery. Seriously. Brett + Bhumy were more then attentive to Bella while we were away, and I loved all the pics and s... (more)"

19. Kristen

Lots of snuggles & Lake walks!

Loop, Chicago, IL, 60605

1 repeat client
5 reviews

"Kristen was great with Wandy! Always updating us with pictures and had dog friends for him to play with too! (He slept all day when he got home) (more)"

Confirmed Memorial Day Availability
20. M Patrick

Dog Lovers For Weekend Sitting

Loop, Chicago, IL, 60605

2 repeat clients
7 reviews

"Both Mike and Amanda were super friendly and reliable. My pup seemed very happy when I picked him up, and he even seemed to have been bathed! They allowed my... (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 Rover.com? 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 Rover.com, 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, Rover.com 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 Rover.com, and stop by our blog to see what we're all about.

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