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.

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

She was great! Took great care of our big, energetic dog. Would definitely book again (more)

from
$30
per visit
Confirmed availability: Labor Day
Michael J.
Active lifestyle-fenced yard!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mike has been taking care of and watching dogs far before he decided to do this officially on Rover. He also dedicates his free time to traveling across the wor… (more)

from
$30
per visit
Calendar Recently Updated
Barbara T.
Caring for favorite family member😊Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

I fully recommend Barbara for all your pet’s needs! She has known my dog Queenie for several years now, and Queenie adores her. Barbara truly has a passion for … (more)

from
$17
per visit
Confirmed availability: Labor Day
Elizabeth S.
Looking to bond with your furry palHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

About: I have lived with dogs and cats my entire life and have walked, fed, and played with animals on a daily basis since I was a child! I'm great with eve… (more)

from
$17
per visit
Calendar Recently Updated
Walter L.
5.
Loving your dogs like my own :)Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

I never have to worry about my dog Juniper when she is with Walter. I love Juniper deeply and want only the best care for her and thats what Walter provides. Ha… (more)

from
$17
per visit
Calendar Recently Updated
Playful, relaxed, and flexible! :DHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Tiffany was so great to our pup Cheeto. He is very anxious around new people, but we always knew we could relax when Tiff is taking care of him. He can tell she… (more)

from
$25
per visit
Calendar Recently Updated
7.
Owner/foster of shy+reactive dogsHyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking
12 years of experience

About: I started volunteering to walk dogs at an animal shelter in 2011. In 2013, I began fostering. I have fostered dogs (particularly shy or reactive), ca… (more)

from
$25
per visit
Calendar Recently Updated
Animal LoverHyde Park, Chicago, IL, 60637
Drop-In Visits, Dog Walking

Allyssa was very communicative before and during her visits with Maya. She was knowledgeable of pet care, so I felt very comfortable leaving my kitty with her. … (more)

from
$20
per visit
Calendar Recently Updated
9.
Caring and experienced dog loverKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

So responsive and followed all instructions perfectly . Was so kind and trusted her with my dog (more)

from
$20
per visit
10.
Loves animals— detail oriented!Kenwood, Chicago, IL, 60615
Drop-In Visits, Dog Walking

I made a last minute booking with Tracie and it was so easy to communicate and coordinate meeting up before hand to meet the cats and share keys. One of my cats… (more)

from
$17
per visit
Calendar Recently Updated
11.
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 greatest ever, seriously. I booked two days beforehand for a family emergency, had to extend my booking twice, and she made everything so easy! Dai… (more)

from
$20
per visit
Confirmed availability: Labor Day
Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

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
$32
per visit
Calendar Recently Updated
13.
Here to give good scratches!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Anna has helped out by taking care of my dogs for the past ten years as a family friend. I was so lucky to have her close to home until she left for school! Wis… (more)

from
$25
per visit
14.
Consistent & Loving :)Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits

Katlyn was wonderful with Miss Ziggy. She visited our cat twice a day, taking care of her. She sent us photo after every visit and a summary of the visit. The p… (more)

from
$25
per visit
Calendar Recently Updated
15.
Responsible, dependable, pet loverHyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Sabrina is an attentive caregiver who has organized schedules to take care of her pets. She is very loving to animals and has looked after several cats in her l… (more)

from
$18
per visit
Calendar Recently Updated
Dog lover/babysitter for your pup!Hyde Park, Chicago, IL, 60615
Dog Boarding, Drop-In Visits, Dog Walking

Where to begin! Madeleine is one of the most genuine, hard-working, humble, accountable, and kind people that I know. Madeleine is engaged and incredibly devote… (more)

from
$16
per visit
17.
energetic, caring dog loverHyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking

I’ve known Viviana for practically my entire life, and she is one of the most responsible and caring people that I know. Throughout school, we often worked tog… (more)

from
$20
per visit
Confirmed availability: Labor Day
18.
Lots of Love to Give your Fur Baby!Kenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Harmony is an amazing pet sitter! She has watched my pets multiple times, for both extended trips and daily care. Harmony was very flexible with her availabilit… (more)

from
$13
per visit
reliable, trustworthy & caring!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Michaela is very good at handling animals and understanding their needs. She is honest, kind, disciplined, and punctual with her appointments. I would trust her… (more)

from
$17
per visit
20.
dedicated and reliable dog-lover!Kenwood, Chicago, IL, 60615
Drop-In Visits, Dog Walking
10 years of experience

About: I’ve had and helped care for dogs all my life! I love dog walks and have fed and walked friends and family dogs for years. I’m currently working par… (more)

from
$20
per visit

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: