House Sitting in Kenwood, Chicago
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1. Emily P.

“Emily has sat for my cat multiple times and is always on time and easy to reach! He warmed up to her right away and I felt at ease during my trip knowing she was there. Will definitely be booking with her again!”


2. Alison F.

“Alison is amazing. She absolutely loves animals and my dog took to her right away. During my travels my dog did not want to leave her side! This is as comfortable as I have ever felt leaving my little one with a sitter. I will be using her exclusively going forward. She is exactly what we all look for when searching for a good sitter. 10/10”


3. Anna O.
“We have used Jackson and Anya many times to take care of our pups and our house. What I appreciate about them is the ease of communication. We travel quite a bit, and it's nice receiving regular updates and photos from them about how things are going. We always find the house clean, plants alive and watered, and the pups happy when we return. Highly recommend.”


4. Zachary S.

“Zachary went above and beyond from organizing a meet and greet before pet sitting to ensuring my house was clean when I came home. He took great care of my dog and I wouldn’t hesitate to leave him with Zachary again.”


5. Brianna S.

“We’ve got one special needs dog and two elderly cats that need very specific diets and medications. We’ve also got one more dog and cat! Brianna came in at the last minute for us to take care of everyone and after getting home it’s clear how much love everyone got from her thank you so much for taking such great care of everyone and sitting for us.”


6. Otis B.

“After a seven night stay, we couldn’t be happier! The dogs seemed happy, we got photos / communication every day, and the house was even left clean. We would use again / recommend to anyone!”


7. Elizabeth D.

“Elizabeth was so great! We were able to meet before the house sitting and went over the specifics of my dog. She gave me daily updates and let me know he was doing well which I really appreciated!! I would definitely book again ?”


8. Michael C.


“Michael stayed with our boy Wrigley for a long weekend and was so wonderful to work with. Our dog is an older boy and needs some special considerations. Michael was so attentive and responsive to Wrigley's special needs. He was also very communicative with us during the stay. I highly recommend Michael as a sitter!”


9. Malcomn F.

“We had an excellent experience with Malcomn while visiting Chicago! He took amazing care of our two large dogs, keeping them happy, exercised, and loved while we were away. I highly recommend him for anyone looking for a trustworthy and attentive pet sitter!”


10. Nicole R.

“Nicole was wonderful! She messaged me everyday on how my dog and cat were doing with pictures or videos. She stayed for like 10 days in our home with them so we are very grateful!”


11. Anais T.

“Anais was very communicative - she sent lots of pictures. She kept the place clean and was respectful. I would book her again. She was accommodating with special needs of my dog.”


12. Connie C.

“Connie was communicative and easily bonded with our dogs! She also sent pictures of them! I felt comfortable leaving my dogs with her and knew they were in good hands. Thank you for taking care of our dogs! Came back to happy puppies!”


13. Brianna J.

“Bre was fantastic watching our Cat! He has some medical that require extra effort/ needs and Bre followed directions and was very communicative in times of doubt. She also took great care of our house. We will hire her again and highly recommend her to watch your pets!”




14. Samantha E.
“Samantha was great! She really saved us when we were put in a bind by a last minute cancellation by another sitter. She sent us daily updates and pictures of our pups, and endured their puppy energy. We came home to a clean house and happy puppies. We would definitely book Samantha again!”


15. Abi S.

“Abi was great with our pups! They were calm and happy when we got back from our trip, and the house was in great shape. Looking forward to the next time.”


16. Dee M.
“Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I know she will get her exercise when she is with Dee. I cannot express enough how much I appreciate Dee & the genuine loving care she gives my little girl, Déjà. Highest recommendations from us!”


17. Carlie R.

“We had the best experience with Carlie! Her and Ani (her pup) stayed at our house for the week while we were on a family trip. Our boy Leo is a Great Dane and she was amazing with him. Not everyone can handle big dogs. I felt at ease with Carlie at our home. I got frequent updates and pictures too! The house was well maintained and in the condition we left it in. 5+ ⭐⭐⭐⭐⭐✨”


18. Molly G.
“Molly has always loved and adored animals. As an adult she cared lovingly for two senior cats with health complications, (one was her own), as well as provided pet sitting for many animals, including a family with two cats and one large dog. This family continues to share with me how much they cherish and appreciate Molly’s time with their pets. Regularly walking dogs is something Molly is dedicated to and enjoys! Molly is highly responsible, trustworthy, reliable and is very caring. She also is creative in her thinking as well as problem solving. These are characteristics which help in working with pets where common issues arise. Molly has a natural gift of being intuitive and empathic towards people and animals, she excels in communication, and she is invested in health and safety. For these reasons, animals often feel safe with her, and they are extremely happy to see her. Animals are also often calm in her presence and thoroughly enjoy her company. As an owner of a pet, you will appreciate Molly’s skills, too. Molly talks with animals reassuringly and after getting to know them, she can read non verbal cueing. When it comes to Molly and animals, they are mutually drawn to each other. It is with great enthusiasm that I highly recommend Molly for pet sitting.”


19. Daniel K.

“Daniel has done an amazing job working with our furry friends. Our dog has lots of special needs and Daniel handles them all without any stress or worry!”


20. Mia L.
“Mia has watched my two cats many times -- each time she has been SO caring and attentive. My cats are picky eaters, and she took extra care when making sure they were fed. She went above and beyond with playing with them and keeping them company while I was gone. She kept me up-to-date on anything that seemed out of the ordinary, but was very self-sufficient and kept contact low but quality high until I returned. I trust her so much with my cats!”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Kenwood.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Kenwood house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
