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.

Active and Accepting Requests (incl. from Essential Workers)
1. Flor Verified Background Check

It will be an adventure with snacks

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Flor has been walking Sagan for many months at this point. Sagan can be difficult (anxious/territorial) and Flor is able to handle her well. We also apprecia... (more)"

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2. Alyssa Verified Enhanced Background Check

Pet lover looking to help ❤️

New City, Chicago, IL, 60609

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

"Alyssa is such a sweet person. She treats every animals, whether it's a fish or a dog, with the most respect. She is very passionate about animals. She makes... (more)"

3. Stanley Verified Background Check

My husky loves energetic friends!

Hyde Park, chicago, IL, 60637

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

About: I have been a dog lover since I could remember! I have had dogs ranging from a small chihuahua to a large cane corso. I currently have a Siberian H... (more)

4. Emily Verified Background Check

Experience with multiple sized dogs

Bridgeport, Chicago, IL, 60616

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

About: I am a student from Chicago currently studying at UIUC. I have lots of free time over the summer and will be able to spend a lot of time and give t... (more)

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5. Elliott Verified Background Check

Marketer by day, Dog lover 4 Life!

Washington Park, Chicago, IL, 60609

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

"Elliot was fantastic! He took great care of our Chow Chow for a week while we were out of the country. She's 11 and can sometimes be a bit temperamental but ... (more)"

6. David Verified Enhanced Background Check

Caring for other's dogs since 1990

Bridgeport, CHICAGO, IL, 60616

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

"David is great! My shy dog can be a challenge, but David became fast friends with him. Reliable, informative — we feel very lucky. (more)"

Active and Accepting Requests (incl. from Essential Workers)
7. Gabriel Verified Background CheckRover 101

Will be cared for like family

Hyde Park, Chicago, IL, 60637

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

"Gabriel is very responsive to requests. We were so happy with his service! Very caring, patient, kind and sent us pictures each day. Thank you for everything. (more)"

8. Indy Verified Background Check

Let me love your dog!

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

"Indy has been walking my two dogs for the past two months and she has been nothing but a god send. She comes by every morning as I leave for work and takes c... (more)"

9. Khala Verified Background Check

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

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

"Khala has been taking care of my pug, Lily Grace, for three years. I trust her completely. Although when I come to pick Lily Grace up, she doesn't always w... (more)"

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10. christine Verified Background Check

Walk and Bark!

Douglas, Chicago, IL, 60616

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

"She was great with my dog! She was reliable and professional! She followed instructions on how to take care of my pup and I would absolutely recommend her to... (more)"

Active and Accepting Requests (incl. from Essential Workers)
11. Marckenley Verified Background Check

Let me take care of your dog

Douglas, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Kenno is by far the best sitter that I’ve had for my dog. He was great about giving updates while I was gone and provided pictures as well. He was great with... (more)"

12. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand 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)"

13. Katja Verified Background Check

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

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

"Katja took great care of my Lola. I could tell by the pictures how happy she was! I really appreciated the detailed reviews, as well. Would book her again! (more)"

14. Sara Verified Background Check

I’d love to take care of your dog

Grand Boulevard, Chicago, IL, 60615

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

"She loves so much animal especially cats and dogs. She loves to play with them. She is a greater person to take care of your pets no doubt. Every pet that sh... (more)"

Active and Accepting Requests (incl. from Essential Workers)
15. Jaya Verified Background Check

Patient & fun dog sitter, Hyde Park

Hyde Park, Chicago, IL, 60637

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

"Jaya was so good with our dogs the two days in Chicago. Close to the house so super convenient. The girls were very calm and happy when they got home. Thank ... (more)"

Active and Accepting Requests
16. Marisa Verified Background Check

Animal lover w/ lots of experience

Hyde Park, Chicago, IL, 60615

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

"Marisa has watched our dog at least once a week since he was an 8 week old puppy. The strongest recommendation we could give would simply be to point out tha... (more)"

17. Samara Verified Background Check

I'd love to take care of your pet

Grand Boulevard, Chicago, IL, 60615

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

"Samara is your perfect dog sitter without doubt! She love animals, especially dogs and cats. She is very responsible and patient. She loves to play and walk ... (more)"

18. Tashara Verified Background Check

Pet sitter with a pet fever

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I am deeply into my spirituality, which makes me deeply connected to nature and animals. I never really have bad experiences with any pets because ... (more)

19. Masheika Verified Background CheckRover 101

Crazy cat lady who loves dogs!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"I was nervous about leaving a newly adopted dog and my 12 year old senior with someone so I did drop in visits and walks. Masheika was great with these two. ... (more)"

20. Kathleen Verified Background Check

Some of the best people I know...

Kenwood, Chicago, IL, 60615

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

"Kathleen G is, seriously, the biggest pet lover I have ever known. She had a wonderful, beautiful dog who passed away last year at age 15. Kathleen cared and... (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: