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. Isabella

Summers off and energetic

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Isabella is the true definition of an animal lover. She truly appreciates animals, unlike anyone I have ever met. Whenever she sees a dog, she rushes over to... (more)"

Available this weekend
2. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

"Adriana is the sweetest girl ever. She is bright, trustworthy and kind. Adriana has always enjoyed coming over to our house to play with our 3 dogs. You will... (more)"

3. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 repeat clients

"Tina did a great job taking care of our two cats while we were out of town for a long weekend! She was very responsive to our requests and was readily availa... (more)"

4. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

5. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

6. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

About: Hello everyone! My name is Breana :). I am currently obtaining my Master's in Speech-Language Pathology. I am reliable, responsible and an animal l... (more)

7. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Simone is a wonderful person and caregiver. Whenever I have Simone petsit for my dog & cats, I am always kept updated on how my babies are doing, and feel 10... (more)"

8. Abby

Experienced Sitter Loves All Pets!

Douglas, Chicago, IL, 60616

Drop-In Visits, Dog Walking

11 repeat clients

"Absolutely excellent! She was available same-day within the hour -- she is awesome. Highly recommended! (more)"

9. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

8 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)"

10. Thandaway

Pre-vet student majoring in cuddles

South Shore, Chicago, IL, 60649

Drop-In Visits, Dog Walking

"Thandaway is my daughter and she has been the owner and care taker of two dogs here at home. She has always loved animals and has decided to make veterinaria... (more)"

11. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

12. Zoe

Experienced and enthusiastic

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Zoe Richters has lovingly cared for my two dogs on many occasions while my family and I have gone on vacation over the past 5 years. She is completely relia... (more)"

13. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"I was traveling out of town for two weeks in January and needed a pet sitter. Rebba was an amazing dog sitter to my beloved Mr. Jinx. She sent me daily photo... (more)"

Available this weekend
14. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Anne texted me each time she was there, even sending updates when our dog had an upset stomach. Thanks Anne for a great weekend of care for our dog!! (more)"

15. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor has taken care of my blue heeler Winston twice while I've been on trips out of the city. She followed my care instructions excellently and I came hom... (more)"

16. Chornodub

home full time and love animals

Douglas, Chicago, IL, 60616

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

About: Hello, my name is Tia. Why I love animals? 1. They are soooo cute!!! 2. They love you as much as you love them. 3. They are a friend. 4. Anim... (more)

17. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

4 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)

18. 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 very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

19. Charlyn

Puppy Dogs and Power walking FTW!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

About: I've been pet sitting and dog walking for a little over 4 years. I care for other people's pets because I can't own my own where I live. I've helpe... (more)

20. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Courtney was great- she was able to come watch my cat over the holiday with short notice! She is extremely friendly and responsible. She sent me updates and ... (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: