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. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"This is the second time Payal cat sits for us! she is lovely with the kitties, communicative and very thoughtful. She checked in on them twice somedays and e... (more)"

2. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Karolina is the best! She house sitted for a long weekend and I'm pretty sure our pup was sad we were back and she had to leave. She walked him a LOT and sen... (more)"

3. India

A Tired Dog is a GOOD Dog!

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"India is an amazing individual. She has a very warm, loving spirit and a kind heart. She helped me tremendously when I needed someone to watch my poodle-mix ... (more)"

4. Lauren

Any and all dogs!

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Lauren is very professional and takes great care of our dog. She is patient with our puppy and we greatly appreciate it. I'm so glad to have her as a trusted... (more)"

5. Debra

Flexible schedule-will run with dog

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Debra is super awesome! She met with before the walk to make sure to hammer out the logistics. I would highly recommend her! (more)"

6. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"Alex is great with the dogs. I feel less guilty in leaving them knowing he is there. They respond well to him and he sends great pictures and updates. I’m... (more)"

7. Joy

Your Dog Will Be Loved!

South Shore, chicago, IL, 60610

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

"Joy is awesome! She was punctual and when I needed her to assist me with my Rupert for an emergency she didn’t hesitate to respond and help. She sent picture... (more)"

8. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

"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)"

9. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

"Enoch is a very responsible sitter! He takes care of my cats very well. Feed them exactly how much it needs to! He plays with them, brushes their hairs and s... (more)"

10. Bob

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)

11. Andrea

Dogs love my peaceful personality!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"We've had several neighbors and family friends bring their dogs for Andrea to sit over the years, and each time she makes their stay comfortable and fun. She... (more)"

12. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

House Sitting, Drop-In Visits

"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)"

13. Laura

Teacher by day... Dog lover by life

Kenwood, Chicago, IL, 60615

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

About: I have been a dog owner most of my life. I currently am dog mom to a beagle mix named spaghetti! She loves to have other dog friends to play with... (more)

14. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

About: Hi! I'm Kat. I am a 22 year old biologist, and I just graduated from BU in Boston and accepted a job at the University of Chicago. My building is p... (more)

15. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Nina took good care of my two cats while I was on Vacation in Florida for a week! She is very reliable. (more)"

16. Alex

I'll take your dog for a run

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"It is clear that a Alex loves animals and he is very responsible taking care of them. We have a dog and a cat that he has taken care of them for years when n... (more)"

17. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"We went away for a several week vacation, and Tom was amazing with our fearful dog. Our dog has a disability, is fearful of strangers in her home, and can re... (more)"

18. Jenisa

Pet Lover- Home Full Time

South Side, Chicago, IL, 60653

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

"Jenisa has a natural way with dogs. They seem to love her instantly. She has cared for my small dogs and my parents large dog for a few years now. Jenisa cl... (more)"

19. James

Dogs are my favorite people!

Hyde Park, Chicago, IL, 60615

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

"James is phenomenal! He’s very professional, patient and loving when it comes to my 2 year old husky. Very dependable. Him and Sam have really formed a great... (more)"

20. Alexandria

LOVE BIG DOGS (especially huskies )

Kenwood, chicago, IL, 60615

Drop-In Visits, Dog Walking

"Alexandria is a sweet girl. She is always available for my dog Benjamin. She takes on long walks and it helps him lost weight cause he is kind of chubb. She ... (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: