House Sitting in Kenwood, Chicago

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

Confirmed President's Day Availability
1. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Harper loves hanging out with Karolina! She is so amazing and helped us even with a weird schedule (switching off between house sitters while we were on an e... (more)"

2. Bridget

I'll love your dog like my own

Near West Side, Chicago, IL, 60661

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

7 repeat clients

"Bridget has stayed with my dog twice now and she has been great. I plan on getting her to pet sit for me more often. My dog recently had surgery on her back ... (more)"

3. Imani

Dogs are friends not food!

Lower West Side, CHICAGO, IL, 60608

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

4 repeat clients

"Imani exceeded expectations. Marlowe was indeed sad to see her go. She was extremely attentive to Marlowe's needs and went above and beyond. This was the lon... (more)"

4. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

22 repeat clients

"Payal watched Nico for us while i was out of town for the day. Needless to say, she did a great job and pretty sure Nico had an awesome time! Payal was ... (more)"

5. Mikayla

Energetic dog-lover

Woodlawn, Chicago, IL, 60637

House Sitting, Dog Walking

2 repeat clients

"Mikayla took good care of our dog alice. She was very responsive to our communications. We would definitely use her again. (more)"

6. Rachel

College student loves dogs!

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Rachel was great to work with. Rachel stayed at my house for the weekend and took very good care of Chloe. She very responsive when I had questions. She was ... (more)"

7. Belicia

I LOVE to play with dogs all day!

Auburn Gresham, Chicago, IL, 60620

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Belicia was an amazing sitter who communicated with us often. She immediately put us at ease by sending us pictures, videos, details regarding every walk, et... (more)"

8. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Scrappy is always so happy when he gets to see Collin and we know he’ll be loved and well taken care of, especially when we have to go out of town (more)"

Confirmed President's Day Availability
9. Stacey

I Love Animals and Animals Love Me

Douglas, Chicago, IL, 60616

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

1 repeat client

"We ( husband, wife and dog) found Stacey very reliable and accessible. The whole experience made our time away stressless. Thanks (more)"

10. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

7 repeat clients

"Allison was an excellent sitter. She was very responsive, proactive, and dependable. She also handled 2 difficult dogs very well. Would highly recommend her ... (more)"

Confirmed President's Day Availability
11. Andrew

Can't wait to meet your Pup!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Andrew regularly texted and sent photos. He was super reassuring that Archie was doing well also and left my house as clean as when he arrived. I would HIG... (more)"

12. Alia

bright smile bright attitude

Grand Crossing, Chicago , IL, 60637

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

1 repeat client

"There is so much to praise Alia for. We in the 2 years our girls, Aae'Vii&Aae'Leha have been on this earth—they've basically only been with My husband and I,... (more)"

13. Amanda

Animal loving college student

Near South Side, Chicago, IL, 60616

Dog Boarding, House Sitting

1 repeat client

"Amanda is experienced and good sitter. She is able to work around the crazy schedules and take good care of my pup (more)"

Confirmed President's Day Availability
14. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"I have come to know Craig as a good and caring person. I have witnessed him interacting with dogs on several occasions and he has displayed genuine concern f... (more)"

15. Nicole

We'll put a Woof over their head!

Near South Side, Chicago, IL, 60616

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

4 repeat clients

"Nicole was awesome! She's a very sweet person and did a great job communicating with us while we were out of the country and put our hearts at ease knowing ... (more)"

16. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

17 repeat clients

"Although Rocco takes a while to warm up to strangers, he was quick to come up to Enoch and wag his little nub at the first meet and greet. That initial meet... (more)"

17. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly went way above and beyond being a good sitter- she was fantastic! She was always prompt, friendly and professional. We received pictures and updates th... (more)"

18. Nicole

Happy to help and flexible schedule

Kenwood, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

About: Grew up with dogs, raised my own, and love 'em to bits! I wish I could keep mine in my apartment, but I am more than happy to help care for yours w... (more)

19. Lily

Diligent student with experience

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"If I would trust anyone with my pet, it would be Lily. She is so responsible and on top of things that I know she would give the utmost care to my dog. Also,... (more)"

20. Lauretta

Friendly and Energetic!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"Lauretta and I have been friends for 10 years now. Throughout those 10 years i've watched as she has grown into the caring, ,compassionate, and loving women ... (more)"


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 eviews from pet owners who have used Rover.