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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1. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jen is awesome, she’s so real and down to earth. She actually cares about my pets (sent me pictures, was willing to work with me when she couldn’t get ahold ... (more)"

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2. Marisa Verified Background Check

Animal lover w/ lots of experience

Hyde Park, Chicago, IL, 60615

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

"I've known Marisa as a dog walker for years and she is great with all sizes and types of dogs. She has also taken care of my dog Pug on multiple occasions. S... (more)"

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3. Kristina Verified Enhanced Background Check

Life is more fun with furry friends

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Kristina and I both worked at Lincoln Park Zoo, a nationally AZA accredited zoo where we served as educational ambassadors to guests of the zoo to educate on... (more)"

4. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

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

"Alicia was great! Our dog is very high energy and is a bit difficult to walk but Alicia handled him great! Would definitely book with her again! (more)"

5. Alexander Verified Background Check

Graduate Student and Animal Lover

Hyde Park, Chicago, IL, 60615

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

"Alex is kind and compassionate to our dogs. He is responsible and truly loves animals. Alex will always go above and beyond to make the dogs are happy. (more)"

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6. Minhyo Verified Background Check

Flexible, caring, and active!

Hyde Park, Chicago, IL, 60637

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

"Testimonial from Rover user (since March 2019) Minhyo is my partner's little sister, and has watched our now 5-month mini goldendoodle on several occasion... (more)"

7. Laura Verified Background Check

Hyde Park dog lady

Hyde Park, Chicago, IL, 60637

Drop-In Visits, Dog Walking

"As Laura's best friend from childhood, I can attest to her love of dogs and dog-walking since she was a kid. Through elementary and middle school, we often w... (more)"

8. Arielle Verified Background Check

Student who needs a dog in her life

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Arielle was friendly, punctual and communicative during her drop in visits with my cat. She provided lots of updates and pictures while I was gone for a long... (more)"

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9. Tenley Verified Background CheckRover 101

Experienced Dog Owner & Care Giver

Douglas, chicago, IL, 60616

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

"Tenley is a wonderful and caring pet owner and caregiver. She has had many pets throughout her life. She recognizes the love and patience it takes to properl... (more)"

10. Ariadne Verified Background Check

An assiduous, punctual dog-lover!

Hyde Park, Chicago, IL, 60615

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

"My dog Sammie and I absolutely love Ariadne! She is always kind and caring, very energetic, and always reliable. Nothing but positive experiences every time ... (more)"

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11. Angelica Verified Background Check

Flexible schedule, love all pets!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Our pup loves her! She treats my dog like he’s one of hers. He is a ball of energy and I’m forever grateful of the care she gives him when I’m away. (more)"

12. Cassidy Verified Enhanced Background Check

I'll treat your fur baby as my own.

Douglas, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cassidy is an excellent and caring pet sitter. She really made my vacation more enjoyable and stress-free knowing that my cat was being taken care of by a de... (more)"

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13. Lilia Verified Background Check

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)"

14. Andrea Verified Background CheckRover 101

Fun times waiting to be had!

Washington Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Andy did a fantastic job befriending my demanding rescue kitty who doesn’t automatically understand people are his friends. Yet while I was away, Andy patien... (more)"

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15. Maeve Verified Background Check

Very open and flexible schedule!

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 vi... (more)"

16. Linda Verified Background Check

Hire this dog lover to love ur pups

Hyde Park, Chicago, IL, 60615

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

"Linda is reliable, kind, responsible and wonderful with our dog. She takes her job seriously, responds well to feedback and instructions and is in general a... (more)"

17. Bob Verified Background CheckRover 101

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

About: A lifetime of experience with multiple dogs and friendly felines, I love both and am here to provide loving care and attention to your furry pet wh... (more)

18. Crystal Verified Background Check

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"I am so happy I found Crystal. It is my second time hiring her to check in on my bunny when I was out of town and she does an exceptional job and I definitel... (more)"

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19. Teylor Verified Background Check

Professional & Fun Dog Handler

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

About: I have over 20+ years of personal experience with all types of dogs but especially large high energy breeds (labs & goldens) ; also cats. Additiona... (more)

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20. Cameron Verified Enhanced Background Check

Your Pet’s Favorite Auntie

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cameron was good with Kona and was helpful on everything and keeping me informed of Kona. (more)"

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: