Pet Sitting & Drop Ins in Kenwood, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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

Search Results

Confirmed availability: 4th of July
Susan C.
1.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan would be a fabulous dog sitter! She has had dogs with special/physical needs, so her compassion knows no bounds. She’s extremely responsible, kindhearted,… (more)

from
$18
per visit
Confirmed availability: 4th of July
Destini E.
Peaches The Pet LoverGrand Crossing, Chicago, IL, 60619
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I Have Two Beautiful Babies Mocha + Midnight Both Pit Breeds But Lovely Individuals They Are Great With Other Pets + People We Have A Park Two Bl… (more)

from
$25
per visit
Calendar Recently Updated
Matt C.
3.
A Pawfect Pet ExperienceKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Matt has stayed with my dog several times. My dog is high energy and requires a lot of ball and play time. Matt rose to the occassion, spending hours outside … (more)

from
$20
per visit
Calendar Recently Updated
Roxy P.
4.
Dogs are a humans bestfriend.Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Roxy was responsive, arrived as scheduled, and checked on our pets as requested. I also appreciate Roxy bringing in our mail packages that were left at the door… (more)

from
$20
per visit
Calendar Recently Updated
Shannon R.
Responsible sitter and animal loverHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Shannon is an extremely reliable, compassionate, caring person. She recently watched my cats overnight when I went out of town, and I felt completely at ease le… (more)

from
$19
per visit
Confirmed availability: 4th of July
All-Day Care for Your DoggoWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I have known Danielle all her life , she has looked after my dog on numerous occasions . Danielle is trustworthy, reliable , friendly and caring she loves dogs,… (more)

from
$15
per visit
Calendar Recently Updated
7.
Love spending time with your petKenwood, Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking

Daniel took care of my puppy when I was out of town and he did a great job! He is very caring and made sure he got tons of attention. It was reassuring to have … (more)

from
$17
per visit
8.
Flexible schedule, big fenced yard!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Maeve was great! Very nice and easy going. You can tell she enjoys animals. Luna love her upon meeting her and her communication was great with photos and video… (more)

from
$20
per visit
Calendar Recently Updated
9.
Over a decade of experience!Hyde Park, Chicago, IL, 60615
Dog Boarding, Drop-In Visits

Kyle was a great sitter! She checked in on Lando every day and sent us updates with photos. We felt that Lando was in safe and caring hands and would highly rec… (more)

from
$20
per visit
Confirmed availability: 4th of July
10.
Ready to greet and treat your pup.Douglas, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Ashley is great with our dog, Shea — I cannot recommend her enough! She cares for my girl as if she were her own. She always goes above and beyond and I never … (more)

from
$20
per visit
Calendar Recently Updated
11.
Animal LoverHyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Allyssa was great with my cats while I was away for the last week. She spent time with them, making sure they had quality timeworn someone, as well as having en… (more)

from
$20
per visit
Calendar Recently Updated
Pets need loving care alwaysKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

This is the first time we had Christina watch our cat. Everything went wonderful! Our cat was very happy, she came on time every day, sent many pictures per day… (more)

from
$16
per visit
Confirmed availability: 4th of July
Vaccinated animal lover. :)Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits

Masheika was wonderful! She communicated great and took care of our cat for over two weeks in our home. We got pictures everyday too! We forgot to cover our cou… (more)

from
$25
per visit
Calendar Recently Updated
14.
Animals are my joy.Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

About: Hello! I have grown up with pets. I've been around them since before birth. Risking sounding a bit antisocial, I'll admit that I love animals more th… (more)

from
$17
per visit
friendly pet care & trainingHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Shaley has experience taking care of dogs of all breeds and ages. She is loving towards the dogs and is very responsible. Shaley cares about all the animals and… (more)

from
$19
per visit
16.
Your Dog Will Love Me!Grand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Alex was amazing. (more)

from
$16
per visit
Hyde Park’s purrfect pet sitter!Kenwood, Chicago, IL, 60653
Drop-In Visits

Victoria has been a fantastic sitter. Reliable, quick to respond, and my cats love her! It's always reassuring to know they are in good hands. (more)

from
$15
per visit
Confirmed availability: 4th of July
18.
Dogs are four legged best friendsGrand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Pamela is a wonderful dog owner and caregiver. She is a yorkie mom and loves to interact and spoil her baby. Seeing her interact with other dogs makes me realiz… (more)

from
$30
per visit
Calendar Recently Updated
19.
Experienced dog lover!Hyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking

Lilia was great!! She took the cutest photos of my cat while I was out of town and took the time to play with her :’) great communication on her end. (more)

from
$17
per visit
Calendar Recently Updated
20.
Sam 
Verified Background Check
Experienced Hyde Park Pet-Sitter!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Sam was fabulous looking after my dog and cat. We came home to happy, healthy pets that were thrilled to see her when we exchanged keys (maybe even more than us… (more)

from
$12
per visit

Rover also offers Pet Sitting & Drop Ins in:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Kenwood, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Kenwood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Kenwood, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Kenwood pet sitters and avoid the kennel.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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: