Pet Setting & 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.

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

2. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

3. Sarah

Life is more fun with a Dog!

Near South Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits

"Sarah is perfect for Rover! She is a great dog mom to her dog Cookie and an amazing aunt to my dog Gary. I rarely trust someone with my little pooch, but wit... (more)"

4. Charlotte

I'll treat your pet as family!

McKinley Park, Chicago, IL, 60609

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

"Charlotte is a wonderful experienced dog sitter! She was willing to humor a very nervous dog mom by sending some very good pictures every day. The instructio... (more)"

5. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

2 repeat clients

"Adriana did a great job when watching my two dogs last week when I was out of town for work. She was reliable, followed all directions, and was very good wi... (more)"

6. Haley

Young Professional Works from Home

Bridgeport, CHICAGO, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Haley has watched my cat for me a number of times when I've had to go out of town. She always does a wonderful job, and sends me updates and photos, so I kno... (more)"

7. Christian

PAWS volunteer,rescuer

McKinley Park, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Christian was awesome and extremely accommodating with such short notice! He came to a meet and greet literally the night before we needed him. He was friend... (more)"

8. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"LeAnna is very professional, and did a great job looking after our little puppy, Isla. She is friendly, fun, and has tons of experience with caring for pets,... (more)"

9. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Our pups love Crystal and I can't imagine a better person to be part of our dog team. So grateful Crystal was able to help. (more)"

10. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Dog Walking

11 repeat clients

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

11. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

18 repeat clients

"Brittany is a very professional and patient sitter. We have a very complicated issue between two cats, they don't get along very well with each other, but Br... (more)"

12. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was great with a little doggie who is mostly afraid of people. Little Jax warmed up to her and she took great care of him. 5 Paws for Moesha (more)"

13. Katie

Pup-loving college student

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've had pets all my life - dogs, cats, gerbils, snakes, you name it! I love animals and would take care of your dog as if it were my own. I love d... (more)

14. Amy

Grad student seeking puppy cuddles

Woodlawn, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Amy was great when I hired her to walk my dog during the day. My dog Bruno loves to walk but also loves to pull. Amy had no problem handling him during the w... (more)"

15. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

8 repeat clients

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)

16. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly took great care of my cats, Fisher and Bugaloo. I appreciated the daily updates and photos. They had plenty of food and water when I returned home. Hig... (more)"

17. Brooke

High energy dog expert!

Bridgeport, Chicago, IL, 60609

Drop-In Visits, Dog Walking

"Brooke is amazing with dogs! Any animals, really. But dogs especially she is great with. She's loving and caring and is a responsible dog owner herself! I wo... (more)"

18. Kelli

The Diva Dog Whisperer

Hyde Park, Chicago, IL, 60637

Drop-In Visits

"Kelli is amazing! She truly cares for dogs and I can tell that my puppies love her. She is always a pro - on time, treats in her pocket and ready for some fu... (more)"

19. Jinni

Skilled Pet Sitter & Photographer

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Although Jinni is my granddaughter and I must admit to being a bit partial, I would recommend her wholeheartedly for dog sitting. She has been an animal lov... (more)"

20. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"Blaize is an excellent petsitter. She's a kind, reliable, and thoughtful person--and a pet-owner herself. You'll have peace of mind when you're away from to ... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

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: