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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Rover 101
Animal Loving FamilyGrand Boulevard, Chicago, IL, 60653
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

I had a great experience. She sent me pictures of my puppy periodically and kept me updated on his status. Her home was very dog friendly and I felt really comf… (more)

from
$40
per night
Calendar Recently Updated
Jaclyn N.
2.
Dogs are my favorite people!Near West Side, CHICAGO, IL, 60608
Dog Boarding, Doggy Day Care

We left our 14.5-year-old Boston Terrier Bruce with Jaclyn for 20+ days this summer. I could not have been more thrilled with her! She took care of Bruce's ever… (more)

from
$39
per night
Ra'eesa S.
Extraordinary pet care! :)Woodlawn, Chicago, IL, 60637
Dog Boarding, Doggy Day Care

Ra’eesa was very professional. First she communicated with me and was open to discussing our first visit to ease my mind. I learned she met with another dog p… (more)

from
$40
per night
Calendar Recently Updated
Madeleine G.
Dog lover/babysitter for your pup!Hyde Park, Chicago, IL, 60615
Dog Boarding, Drop-In Visits, Dog Walking

I’ve used her several times now. She’s always been amazing. She sends me pictures and updates. As a added bonus my dog gets to do yoga and go to the lake. Love … (more)

from
$40
per night
Calendar Recently Updated
Michael C.
Special Needs & Senior SpecialistHyde Park, Chicago, IL, 60615
Dog Boarding

My dog had a wonderful time with Michael and his dog Cal! Michael did a great job of keeping me up-to-date to ensure I wasn't worried during her first overnigh… (more)

from
$45
per night
Calendar Recently Updated
6.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan is the best. She regularly kept us updated and sent photos. She gave us a thorough out brief as to what, if anything is going on with my fur babies. I loo… (more)

from
$50
per night
Calendar Recently Updated
Active lifestyle-fenced yard!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We loved leaving both our Giant Schnauzers with him for the weekend. He would send us updates and pictures. When we picked up our dogs, they looked very comfort… (more)

from
$45
per night
Calendar Recently Updated
8.
I Give All the Pet and Cuddles!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Sarah has looked over our pup Bear multiple times over the years. He is a special needs dog because he had a torn acl, so he needs meds and specialized therapy… (more)

from
$40
per night
Calendar Recently Updated
9.
Only one who showers selfless loveDouglas, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

A warm and welcoming sitter! We had to cut our stay short, but she took very good care of Bruno. She is very responsive and maintains good communication. Highly… (more)

from
$40
per night
Dog people are good peopleKenwood, Chicago, IL, 60653
Dog Boarding

Great Family. My dog loved them immediately at our meet & greet. Steve 7 Monica sent photos of my dog where he seemed to be smiling ;-). I was very comfortable … (more)

from
$40
per night
Confirmed availability: Labor Day
11.
Fun family to care for your dog!Bridgeport, Chicago, IL, 60609
Dog Boarding

Mary was absolutely amazing! My dog ended up being sick while I was away on vacation and Mary provided so much care and love for her! She is great at communicat… (more)

from
$45
per night
Calendar Recently Updated
12.
I treat all pet like my own petBridgeport, Chicago, IL, 60616
Dog Boarding, Doggy Day Care, Dog Walking

Is very flexible with drop off time and very friendly! Gave us plenty of updates and pictures of our little ones so we knew they were having fun and well taken… (more)

from
$45
per night
Confirmed availability: Labor Day
13.
NOT A PET, A FAMILY MEMBERLower West Side, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

Your dog will be in such good hands with David! I have a rescue pup, who is apprehensive/lunge-y with men in particular and can be particular with other dogs. W… (more)

from
$40
per night
Confirmed availability: Labor Day
14.
Your pups new favorite Auntie!Near South Side, Chicago, IL, 60616
Dog Boarding

She is now auntie Marjani!! I was able to leave Tiger in great hands, I'm a bit jealous because he was loving on her more than me, his cat mom. (more)

from
$60
per night
Calendar Recently Updated
15.
Experienced Dog Owner and Dog LoverNear North Side, Chicago, IL, 60654
Dog Boarding, Doggy Day Care

Second time booking with Melanie: Max loves staying with Melanie and is always excited to stay with her. I also appreciate the daily photos/updates. Melanie is … (more)

from
$45
per night
16.
Woman boss and a bark of a hustleHyde Park, Chicago, IL, 60615
Dog Boarding, Doggy Day Care, Dog Walking

Ashley is very professional, gives great updates about your pup, and takes the job of caring for your pet seriously! 10/10, would strongly recommend. (more)

from
$45
per night
Confirmed availability: Labor Day
17.
Work from home | Treats. Play. ♥️Loop, Chicago, IL, 60607
Dog Boarding, Drop-In Visits, Dog Walking

Alison did an amazing job! She sent daily photos and updates, and she made the entire drop off/pick up process super easy. Highly recommend!! (more)

from
$80
per night
Your fur baby will be in good handsGrand Crossing, Chicago, IL, 60619
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Left my cooper with Nakeisha while I went on vacation and my pup came back happy and well. I loved that I was getting updates throughout the day and was able to… (more)

from
$55
per night
Calendar Recently Updated
19.
Work from home/flexible pet sitter!Near North Side, Chicago, IL, 60654
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Brandon and Brittany were a wonderful sitters for Lulu! Brandon took her to the park and let her run with other pups and kept me updated with photos at least tw… (more)

from
$65
per night
Calendar Recently Updated
Your fur baby's new best friends!Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Monica & Calvin took great care of my grumpy, old little guy! I booked them sort of minute over the holidays, and it was such a relief to know my dog would be i… (more)

from
$48
per night

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: