House Sitting in Kenwood, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

1. Frances

Compassionate, Fun Loving & Active

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Frances was great with my two crazy dogs!! This was my first time using Rover and Frances stayed in my house to watch my two big and rambunctious dogs. It i... (more)"

2. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin was fantastic. Super professional, communicative, and very caring. Lulu and Bolt loved him. I felt very comfortable and confident that my pups were in... (more)"

3. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

5 repeat clients

"Allison is hands down the best pet sitter! We had her stay in our home over a long weekend with our two senior pups. She provided excellent communication and... (more)"

4. KC

Loving Pet Sitter/Nursing Student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"KC watched our 4 month old puppy, George, while we were away for the first time since we brought him home. I was so nervous leaving our little guy behind, bu... (more)"

5. Kat

Quality care for our fur babies

Lower West Side, Chicago, IL, 60608

House Sitting

"Kat has been the best dog sitter I have came across. It is most important for me to find a trustworthy, responsible and friendly person, and Kat is exactly t... (more)"

6. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Our experience with LeAnna was wonderful! She took perfect care of our dog and cat and kept us updated throughout the stay. She really listened and We are co... (more)"

7. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Dog Walking

6 repeat clients

"This was our first time hiring a pet sitter and Catherine was amazing! Both animals were well taken care and we could not be more pleased! Will definitely be... (more)"

8. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I could not have asked for a better sitter than Crystal. She came over prior to the start of service to meet my dog and I could tell at once that she was tru... (more)"

9. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

10. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Emily was great. She picked our dog up early to help us with our travel arrangements, she sent lots of photo updates and checked in frequently. I felt like m... (more)"

11. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

12. Krista

Flexible schedule, love dogs

Hyde Park, Chicago, IL, 60615

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

About: Other dog owners describe me as a caring, responsible, loving dog lover and pet sitter. I'm a current grad student so I have a flexible schedule to... (more)

13. Phoebe

Lots of availability - Lots of love

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Phoebe was really great with the dogs. Totally competent and completely trustworthy. I have two older dogs, one is a very picky eater who usually loses a t... (more)"

14. Mary

Mary's Pet Care

South Side, Chicago, IL, 60616

House Sitting

5 repeat clients

"Mary was great and I never had to worry about my dog while I was away. This was Mary's second stay with Sergio and again she sent pics and updates every day,... (more)"

15. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor is the best!!! I have never been so at ease leaving my dog with anyone until Eleanor came into the picture. I received daily updates and pictures w... (more)"

16. Myk'La

Mind, face, and soul of a pup

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

17. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"Alexandra was a hit with juno right off the bat. She was super helpful with a last minute booking!! Definitely will be looking to book her again!! took amazi... (more)"

18. Sydney

I am energetic and attentive!

Grand Boulevard, chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sydney is a very intelligent, responsible young woman. She has a passion for animals and been around dogs and cats all her life. (At one time, living with 3 ... (more)"

19. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

3 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)"

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

Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.