Dog Boarding in Kenwood, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Stella is super energetic and fun loving which can sometimes make her a handful. Despite that, Jennifer did a great job keeping Stella happy, engaged with to... (more)"

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2. Khala

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

Dog Boarding

"Khala has been so fantastic. On our 2nd time with her I couldnt drop off Major, and she came to pick him up. He was beyond thrilled to see her!! We are so lu... (more)"

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3. Janet

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding

"I recommend Janet for your pet sitter needs. She was very friendly and kept me updated each day with photos and daily updates. She also is quick to reply t... (more)"

Confirmed availability
Christmas and New Year
4. Terry

I love dogs and Love to be outside

Near South Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Terry was quick to respond and was wonderful with our big, energetic boy. I couldn’t be more pleased with the whole stay. (more)"

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5. Ekaterina

Home full-time - small fenced yard

Bridgeport, CHICAGO, IL, 60608

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Kat was absolutely wonderful. From the initial meet and greet she was able to set my mind at ease about leaving my Jax with her. Her friendly, caring persona... (more)"

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6. Catherine

I’ll nurture your furry best friend

Hyde Park, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Catherine was lovely to work with. She provided excellent care of Freddy, and even did a little training with him. She really tried to accommodate his indivi... (more)"

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7. Saroja

Work from home; dog run in building

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

"Saroja was a great sitter! Our pup came home happy and well cared-for. On top of that, she was flexible when we ran into some travel problems, which was very... (more)"

Confirmed availability
Christmas and New Year
8. Jen & Dakota

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"Jen was so great with my two! She communicated with me so well & I could tell from photos they had a great time! I will definitely use her again! (more)"

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9. Jasmine

Plenty of long walks and treats!

Bridgeport, Chicago, IL, 60609

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"My dog, Willow, seemed to enjoy staying with Jasmine, and everything seemed to go well. Jasmine sent photos during those few days we were gone. I would rec... (more)"

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10. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

Dog Boarding, Doggy Day Care, Dog Walking

"Dwight was an amazing host for our little buddy Arthur! He was communicative and flexible in drop-off and pick-up times, and sent some lovely photo and text ... (more)"

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11. Zak

Home all day - fenced yard

Douglas, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Zak did an amazing job with Golfo! He sent me a lot of pictures and always updated me on what they were up to! I’m sure golfo had a lot of fun and I would to... (more)"

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12. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Marga and her roommate have taken amazing care of our dog when we've had to leave town. Both times, they've taken him not just on walks but on outdoor advent... (more)"

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13. Irema

The most attentive doggo lover

Hyde Park, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I have known Irema since high school and she is an amazing dog owner and caregiver. She is always excited to help dogs feel special and loved. Irema board... (more)"

Confirmed availability
This weekend
14. Cassidy

I’ll run with your dog

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Cassidy grew up on a dairy farm and has cared for a variety of animals - from millipedes to cows! She has always lived with dogs and cats and has an uncanny... (more)"

15. Jennifer

I love long walks at the park.

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

"I was nervous leaving Lilly with someone I did not know instead of boarding her. When Lilly and I met Jennifer, she was so sweet, kind, and loving towards Li... (more)"

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16. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

"We were in Chicago for just a couple of days and wanted our pup to have fun while we were off having fun and boy did he!! When we met Craig and his dogs, my ... (more)"

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17. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Alex did a wonderful job taking care of our dog in his house. He provided lots of updates with photos and was very accommodating. He took great care of our d... (more)"

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18. Breanna

F/A saving dogs around the world!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Breanna was just amazing with our dogs! Sent us updates, pics and even a video. She was very accommodating, and took on two new clients (Sasha and Drexel) fo... (more)"

19. Kyle

Flexible hours - love walking dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Kyle took great care of my dog Maggie! He was quick to respond, sent lots of updates, and was very flexible with drop off/pick ups. My new go-to when I need ... (more)"

Confirmed availability
This weekend
20. Dena

Doggy Spoiler Alert

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits

"Dena was a life saver! Amazingly convenient and in my area. It's especially hard to find someone who is willing to care for a pitbull but she was more than a... (more)"

Dog lovers in Kenwood, Chicago, IL love dog sitters on Rover.com. Over 7,915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com is the simple, savvy way to find and book Kenwood dog boarding. It's easy to find the perfect dog sitter. Many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book dog boarding on Rover, your dog will enjoy a loving staycation in their sitter's home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter in Kenwood, Chicago, IL has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 75,000 sitters who've listed their services on Rover. When you book Kenwood dog boarding on Rover, your dog gets the loving care they deserve, and you get peace of mind.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

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 Kenwood, 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 organizations across the nation, including: