House Sitting In Kenwood

Find a loving house sitter to watch over your pets and your home.

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Top rated Kenwood house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Nicole D.
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Nicole D.
Star Sitter
from
$60
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Chicago, IL, 60602

Nicole is so sweet and communicative! She was quick to respond from the first message I sent her inquiring about her availability. She took good care of our pups and would be happy to have her watch our girls again!

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Kellyn C.
Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$35
per night
4.9 out of 5 stars
17 reviews
2 repeat clients
5 years of experience
Hyde Park, Chicago, IL, 60615

Lucille was a fantastic sitter and our dog had a blast. She was so thoughtful about making sure our dog Lea felt comfortable, and she kept us updated with great photos and videos.

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Karlos B.
Sitter Profile Image: Jade T.
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Jade T.
Star Sitter
from
$70
per night
5.0 out of 5 stars
52 reviews
13 repeat clients
11 years of experience
Lower West Side, Chicago, IL, 60608

Jade was wonderful and loving with our dog and respectful of our home. This was our first experience with a dog sitter. It was amazing and we would definitely have Jade sit for us again!

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Alicia G.
Sitter Profile Image: Annie X.
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Annie X.
from
$65
per night
4.9 out of 5 stars
156 reviews
113 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

Annie watched our French Bulldog, Fiona, for 7 days. It was also a holiday weekend which is a big deal. She did a great job with Fiona! She would send pictures and Fiona looked like she was in her element at home. I felt so comfortable with Annie taking care of Fiona that I didn't feel the need to check in constantly (which is a big thing for me). She also left the apartment just as clean as we had left it! She was great!

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Brooke S.
Sitter Profile Image: Andrea W.
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Andrea W.
from
$30
per night
6 years of experience
Kenwood, Chicago, IL, 60615

About: I am experienced in very detailed pet care instructions and understand that those pets have unique needs. I have experience with administering medical supplements, adhering to specific feeding schedules and portion requirements. I have followed individualized activity plans and routines for both dogs and cats. I want to provide the consistency in a pets routine while their owners are away. I promote owner-established potty training methods in regards to 6 months and older potty training behaviors. My approach combines reliability, patience, and genuine affection for animals while providing pet owners with confidence that their pets are receiving attentive and compassionate care in their absence. I am a Retired NCAA WBB coach so I have time to care for your fur family! I Can adjust to your pets favorite routine! I stay in your home so that your fur family is in their most safe space! I stick to their routines and routes! I can include new enrichment activities and stick to what works for them! I understand crating and routine! I have also slept w 4 animals in bed so that were very supported during the owner’s mini vacation.

Sitter Profile Image: Zoe R.
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Zoe R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
10 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60615

Zoe watched our sweet pup and her cousin for an evening. She was on time (early), friendly, and sweet.

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Colleen S.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$35
per night
5.0 out of 5 stars
26 reviews
12 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Jozelin did a great job with our two cats. Lots of pictures of them hanging out together. She left everything in order after her stay at our place, and we will definitely book with her again.

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Charles K.
Sitter Profile Image: Bella B.
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Bella B.
from
$40
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60615

Bella did a great job with our pups. Great communication and she was very flexible working with our pack. I'd gladly have her back to watch them any time.

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Andrew M.
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
43 reviews
15 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
Sitter Profile Image: Rachelle S.
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Rachelle S.
from
$65
per night
4.9 out of 5 stars
50 reviews
14 repeat clients
9 years of experience
Near South Side, Chicago, IL, 60605

Rachelle and her husband did a wonderful job taking care of our senior girls when we were out of town for the weekend! Really appreciate all their updates/making sure both girls got their medications

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Valeria V.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$45
per night
5.0 out of 5 stars
30 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

Elizabeth took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.

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Jenny L.
Sitter Profile Image: Claire P.
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Claire P.
from
$70
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
Sitter Profile Image: Mia L.
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Mia L.
from
$45
per night
5.0 out of 5 stars
26 reviews
5 repeat clients
7 years of experience
Hyde Park, Chicago, IL, 60615

Mia was incredible with my cat Stormie! We were able to quickly schedule a meet and greet for her to meet Stormie and I could already tell she genuinely cared. She asked questions about feeding, whether Stormie likes to sleep in the bed, daily routine, and took notes when I explained some food changes due to Stormie's sensitive stomach. It is VERY clear she does truly love and care for animals. We had Mia watch Stormie for the weekend and came back to the apartment being clean, litterboxes were empty and freshly cleaned, etc. Mia sent regular updates as well with photos and videos of Stormie so I knew that everything was going smoothly. She also sent messages regularly about how they were playing with toys, how Stormie was doing, etc. I 100% will book with Mia again as I truly never felt more comfortable with someone watching my baby before now.

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Lillian W.
Sitter Profile Image: Bipasha R.
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Bipasha R.
from
$50
per night
5 years of experience
Kenwood, Chicago, IL, 60615

About: Hi! My name is Bipasha, and I’m currently a first-year med student here in Chicago. I miss my dog, Cody, so very much and would love to spend some time with your dog(s)! I am available for both dog sitting and dog walking. I am doing work remotely from June to August and have plenty of time and flexibility to help with pet care in the Chicago area. I currently live in an apartment so can only take care of pets in the owner’s home. I am very clean and reliable, and will be sure to take great care of your home and pet!

Sitter Profile Image: Jasmine P.
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Jasmine P.
Star Sitter
from
$175
per night
5.0 out of 5 stars
97 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

Jasmine was amazing! She showed great compassion toward our pups and responsiveness to our concerns. One of dogs had GI symptoms from the start of her visit. Jasmine monitored closely and took our pup to the emergency vet for us (the pup is fine 😊)… this was an unexpected snag that took a lot of time and care. But Jasmine did it willingly and kept us informed throughout. We will definitely hire her again!!! (Oh! And she did a great job taking care of the house too!)

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Stephanie P.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
30 reviews
6 repeat clients
1 year of experience
Chicago, IL, 60616

Emily was great! She followed directions closely and took great care of Levi while I was away. It was wonderful to come back to a clean home and a happy dog. I would definitely book her again in the future.

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Jasmine J.
Sitter Profile Image: Ava M.
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Ava M.
from
$55
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
11 years of experience
Hyde Park, Chicago, IL, 60637

Ava was wonderful with our 3 pups. She knew how to manage their chaos and treated them so sweetly. She left the place looking great and really just went above and beyond. We will definitely be using her services again.

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Gail S.
Sitter Profile Image: Nikki J.
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Nikki J.
Star Sitter
from
$45
per night
5.0 out of 5 stars
35 reviews
10 repeat clients
15 years of experience
Kenwood, Chicago, IL, 60615

Right off the bat I got an excellent first impression of Nikki. She is very warm and friendly. She approached my cat slowly, allowing the greeting to be on my cat’s terms. It showed me she understood cats. During the stay she sent pictures and updates which put me at ease. Nikki was extremely flexible with booking times. When I got home my linens and towels were clean which was not requested or expected. She really above and beyond! She’s now my go-to gal! If you’re looking for someone kind, communicative and great with animals… well, look no further!

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Allie K.
Sitter Profile Image: Quinn W.
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Quinn W.
from
$65
per night
5.0 out of 5 stars
10 reviews
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

Quinn was fantastic. She was very responsible, and our dog, who can be a lot of work, loved her. She stayed with our dog at our home and was very neat and responsible. I highly recommend her!

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Sara E.
Sitter Profile Image: Maya C.
Verified Enhanced Background Check
Maya C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
112 reviews
44 repeat clients
8 years of experience
Kenwood, Chicago, IL, 60615

Maya did an incredible job and our 4 month old puppy absolutely loved her. Very kind and knowledgeable. Took the initiative to incorporate training during his walk and play time. Provided pictures from throughout her stay. Extremely thorough. M

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Joel T.
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Kenwood pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Alexis did a wonderful job looking after my energetic, large dog while I was away. She sent many photos and updates and took wonderful care of my pup and home. Would definitely hire again and recommend to anyone

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Reanna N.
House Sitting
5.0 out of 5 stars

Allison has been an amazing dogsitter for our dog, Max. This is the third time we’ve worked with her, and she continues to exceed expectations every time. She’s reliable & communicative, and most importantly Max is always happy and well taken care of when we return. It gives us real peace of mind knowing he’s in such great hands. Highly recommend Allison!

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Gary T.
House Sitting
5.0 out of 5 stars

Jozelin took great care of our dog, Derby. She was communicative and responsive and sent us great photos of Derby while we were on vacation. I would recommend booking Jozelin to care for your pets!

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Kaylyn T.
House Sitting
5.0 out of 5 stars

Rahmya was amazing! She was very flexible in setting up a meet and greet and instantly prioritized befriend Stormie. I got lots of updates and update pictures daily of stormie which made the whole process of being out of town much easier. I never felt like Stormie wasn't in good hands. The home was clean and perfectly tidy when we arrived back, which was so appreciated when returning from our trip. I would 100% recommend Rahmya for anyone looking for a pet sitter 💙

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Lillian W.
House Sitting
5.0 out of 5 stars

Our pups felt comfortable right away. Clearly a dog lover and can read their body language. Thank you again!

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Tommy H.
House Sitting
5.0 out of 5 stars

Hired Maia again for another weekend of house sitting. Very responsible and respectful of taking care of the house and the pup. My puppy gives her 5 paws! Thank you Maia, I won't need to ever hire any one else!

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anhri89@yahoo.com
House Sitting
5.0 out of 5 stars

Bri does an absolutely incredible job! My dogs are obsessed with her and she send the best pics. She has also taken care of several issues w my house while she was house sitting. She is responsible and trustworthy, 100% recommend!

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Kate B.
House Sitting
5.0 out of 5 stars

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
House Sitting
5.0 out of 5 stars

Annie was amazing! I am so thankful for her kindness to my three animals (two cats and a dog). She was so attentive, communicative, and caring, following all of their care routines by the book! Her love of animals is very apparent. I highly recommend her and will definitely be using her again. Thank you Annie!

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Veronica M.
House Sitting
5.0 out of 5 stars

Lucille is an incredibly kind and attentive cat sitter. She made him feel loved and played with him so much. She even took him for a stroll on his backpack. Would highly recommend. Felt like our baby was in wonderful hands!

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Joanna A.
House Sitting
5.0 out of 5 stars

Mia was incredible with my cat Stormie! We were able to quickly schedule a meet and greet for her to meet Stormie and I could already tell she genuinely cared. She asked questions about feeding, whether Stormie likes to sleep in the bed, daily routine, and took notes when I explained some food changes due to Stormie's sensitive stomach. It is VERY clear she does truly love and care for animals. We had Mia watch Stormie for the weekend and came back to the apartment being clean, litterboxes were empty and freshly cleaned, etc. Mia sent regular updates as well with photos and videos of Stormie so I knew that everything was going smoothly. She also sent messages regularly about how they were playing with toys, how Stormie was doing, etc. I 100% will book with Mia again as I truly never felt more comfortable with someone watching my baby before now.

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Lillian W.
House Sitting
5.0 out of 5 stars

Phenomenal. Anais took great care of our doges and home. She was extremely responsive to our messages and sent update pictures every day.

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Gabriel L.
House Sitting
5.0 out of 5 stars

Diana did an amazing job watching my dog while I was away. Highly recommend for your pet sitting needs.

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Jommel M.
House Sitting
5.0 out of 5 stars

He was so amazing!! Followed all of my puppy’s care instructions perfectly. I felt very comfortable leaving her with Xavier. I am definitely going to be rebooking with him soon!

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Catie K.
House Sitting
5.0 out of 5 stars

Jasmine is the epitome of caring combined with professionalism. She took care of my small shorkie for an extended stay and when i returned my pet was calm and well cared for. Jasmine checked in every day with a quick message update and pics to let me know how things were coming along. She even checked in on the plants as well. Highly recommend this sitter and will use her again

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yvonne b.
House Sitting
5.0 out of 5 stars

Dahlia was fantastic to work with. She was great at communicating and sent daily updates of our pups while we were out of town. I felt confident our pets were well cared for. She was respectful of our home as well. I would definitely recommend Dahlia for any housesitting and pet needs.

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Sarah H.
House Sitting
5.0 out of 5 stars

Ahriel housesat for us for 15 days over the holiday to care for our Boston Terrier, Millie. Ahriel was very professional, responsible, and reliable. Ahri was thoughtful in her questions during the meet and greet and Millie liked her immediately, which isn’t always the case. While we were away, she communicated regularly with us in line with our agreed frequency, sending photos and making note of anything concerning. She stayed at our home while we were away and left it clean and exactly as it was when we left (maybe better?). Millie is happy and healthy! I would highly recommend Ahri and will always check her availability for future sits!

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Erin L.
House Sitting
5.0 out of 5 stars

Marlicia is the best!!! She is a wonderful dog sitter and home sitter as well. My husband and I have used her three times now and will continue to do so whenever possible, she is attentive to the dogs schedules and routines, sends multiple updates and is always easy to get a hold of if needed. We can tell our dogs enjoy their time with her as well, when we come home they are relaxed and happy, which is truly the piece of mind we need. She also has had to manage random scenarios that came up and is so go with the flow. For example The first time we used her services she had to facilitate our movers dropping off all our stuff while we were on a cruise and not reachable for some time 😱 she also even gave us a present when we came back from our wedding trip, which meant a lot to us! she is excellent at long stays as well, all three times we have had her stay with the dogs we were gone for 8-10 days. Plus she is able to walk our 90lb Doberman and 50lb Aussie at the same time (not easy to do at all!) and we could tell she had experience with all different dog breeds and sizes. I cannot recommend her enough!

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Alyssa B.
House Sitting
5.0 out of 5 stars

Laurel was so sweet and dog sat for us while we were in Chicago and we couldn’t be more pleased with the experience. I wouldn’t hesitate to book with her again and I think Gram would say the same. :)

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Miranda H.
House Sitting
5.0 out of 5 stars

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Kenwood house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

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.