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

Drop-In Visits, Dog Walking

5 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. 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)

3. Bri

I like dogs more than people.

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Brianna is amazing with others especially with animals very caring and wants the best for the people she cares about . I've enjoyed working with her over th... (more)"

4. 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)"

5. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

6. Phoebe

Lots of availability - Lots of love

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Phoebe took excellent care of our Pomeranian while we spent our annual week at Disney World. It seemed like she and Moxie really bonded - we felt like we lef... (more)"

7. 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)"

8. 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)"

9. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

2 repeat clients

"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)"

10. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

9 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. Katie

Pup-loving college student

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

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)

12. Audrey

Dogs are my life!

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Audrey is great with animals. She is very caring and experienced with animals. I've seen Audrey take wonderful care of her pet cat. She has grown up aroun... (more)"

13. Brooke

High energy dog expert!

Bridgeport, Chicago, IL, 60609

Drop-In Visits, Dog Walking

"Brooke is awesome and genuinely loves to care for animals. She has always been a huge animal lover and puts their needs and desires above her own. I would tr... (more)"

14. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"Rebba is incredibly compassionate and loving with dogs. She genuinely cares for them and showed great kindness and care for my late dog. Your dog will be i... (more)"

15. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

9 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)"

16. 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)"

17. Billie

Experience, love and care

Grand Boulevard, Chicago , IL, 60653

House Sitting, Drop-In Visits, Dog Walking

About: I am a client care coordinator at a well established veterinary practice. In addition to working with dogs and cats on a daily basis, I have had pe... (more)

18. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

7 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)

19. Jenna

Caring Fur Mommy

Hyde Park, Chicago, IL, 60615

Drop-In Visits

"Jenna is an amazing dog-mommy! She goes above and beyond to make sure that her pups are happy, healthy, entertained, and stimulated. She has fostered pups fo... (more)"

20. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

5 repeat clients

"Allison is fantastic. We use her as often as we can for Eli and Sydney. She goes above and beyond in all aspects and the dogs love her as well. We couldn't a... (more)"

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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: