House Sitting in Kenwood, Chicago

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

Search

More resources

RoverProtect

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more

Loving house sitters in your neighborhood

Search Results

Sitter Profile Image: Otis B.
Verified Background Check
Sitter Profile Image: Otis B.
Verified Background Check

1. Otis B.

Dog's Best Friend
Loop, Chicago, IL, 60602
5.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5.0 out of 5 stars
65 reviews
28 repeat clients
Profile image

I highly recommend Otis as a Rover sitter! He was very punctual and professional during our meet and greet. During his stay in my home, he followed all instructions - including correctly using a type of leash that was new to him - and sent lots of updates and photos. I will definitely book Otis again in the future!

Availability updated today
Sitter Profile Image: Belicia K.
Verified Background Check
Sitter Profile Image: Belicia K.
Verified Background Check

2. Belicia K.

Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
14 reviews
7 repeat clients
Profile image

My cat sitter cancelled on me at the last minute. But as it turns out I was meant to find Belicia. She took excellent care of my girl Zuri. Belicia was communicative, kind, and followed all instructions. She sent me messages and photos to absolve any worry and it didn't take long for my anti-social kitty to take to her. Having her care for Zuri was such a peace of mind. When I came back home, I realize that everything worked out as it should have. This is the beginning, as I will be scheduling with Belicia again.

Availability updated 8 days ago
Sitter Profile Image: Deven S.
Verified Enhanced Background Check
Sitter Profile Image: Deven S.
Verified Enhanced Background Check

3. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
54 reviews
16 repeat clients
Profile image

Deven is great! He took care of Lilith for more than 3 weeks and kept us updated regularly. He sent photos and FaceTimed us, took her on walks and got her pup cups. Made our time away from our baby better and less worrisome. We definitely recommend Deven! He even stayed late on the last day cause my flight was delayed and I needed him to take care of Lilith a bit more.

Availability updated 15 days ago
Sitter Profile Image: Emily N.
Verified Background Check
Sitter Profile Image: Emily N.
Verified Background Check

4. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
145 reviews
42 repeat clients
Profile image

Emily was, as usual, an AMAZING dog sitter for Finn for the week we were gone. She is kind, attentive, and professional. She plays with Finn and sends detailed updates. She was very flexible and updated us via WhatsApp because we were out of the country. We will always come to her first if we need a sitter for Finn!

Availability updated 9 days ago
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check

5. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
Profile image

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 ?

Availability updated 11 days ago
Sitter Profile Image: Alexa B.
Verified Enhanced Background Check
Sitter Profile Image: Alexa B.
Verified Enhanced Background Check

6. Alexa B.

200ccs of love and affection = me
Chicago, IL, 60619
4.5 mi. away
House Sitting, Dog Walking
from
$50
per night
5.0 out of 5 stars
4 reviews
Profile image

Alexa did a wonderful job taking care of our dog in our home over a long holiday weekend. She was communicative, made sure Beau got his walks and play time, left our home clean and our dog happy. She followed our instructions on everything and asked questions when she wasn’t sure about something. We hope our dog wasn’t too crazy for her, but we would gladly welcome her back! So grateful we found Alexa.

Availability updated 2 days ago
Sitter Profile Image: Margo K.
Verified Enhanced Background Check
Sitter Profile Image: Margo K.
Verified Enhanced Background Check

7. Margo K.

Animal lover living in Bridgeport!
Bridgeport, Chicago, IL, 60608
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
4.0 out of 5 stars
7 reviews
Profile image

Margo did a great job. She was flexible and responsive. She sent lots of pictures and updates of our cats. We returned home after a week-long vacation and the house was in excellent shape. I will definitely use her for house-sitting and drop-in services in the future.

Availability updated 56 days ago
Sitter Profile Image: Nicole R.
Verified Enhanced Background Check
Sitter Profile Image: Nicole R.
Verified Enhanced Background Check

8. Nicole R.

Lovable reliable & trustworthy!
Bridgeport, Chicago, IL, 60616
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
Profile image

This our first time hiring someone to take care of our dogs, usually we leave them with family. This time the entire family was on a trip so we opted for Rover and feel very blessed to have found Nicole. Nicole is very detail-oriented, communicated perfectly and even sent videos twice a day. We decided to leave the dogs at home instead of sending them to an unknown environment. And she not only walked them. She sat with them and gave them attention. This all became very crucial because it was very hard for me to leave my dogs this time around. One of my dogs had a bit of an eye irritation and she did a great job keeping track of his progress and keeping me updated. We are very grateful for Nicole and will definitely ask for her services again in the future.

Availability updated today
Sitter Profile Image: Shakira C.
Verified Background Check
Sitter Profile Image: Shakira C.
Verified Background Check

9. Shakira C.

RoverGO
Rover 101
Star Sitter
Your Pup is My Pup
South Shore, Chicago, IL, 60649
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
41 reviews
7 repeat clients
Profile image

Shakira is the absolute best and just a amazing lady! This was my first time hes I g him with a stranger. Both she and Benzo fell in love with each other and he was looking sad when she left. She took good care of my boy and kept me updated on his activities during the day. Couldn’t ask for a better experience or sitter for my puppy. Do not hesitate ti book her if she’s available; you won’t regret it I promise. She is a dog whisperer!!?

Availability updated 4 months ago
Sitter Profile Image: Sarah S.
Verified Background Check
Sitter Profile Image: Sarah S.
Verified Background Check

10. Sarah S.

Rover 101
Experienced Animal Care
Bridgeport, Chicago, IL, 60609
2.7 mi. away
House Sitting, Dog Walking
from
$60
per night
5.0 out of 5 stars
58 reviews
12 repeat clients
Profile image

Sarah took very good care of our 3 spoiled babies, and took care of our house. We recommend her and will definitely be using her again in the future!!

Availability updated 5 days ago
Sitter Profile Image: Abi S.
Verified Enhanced Background Check
Sitter Profile Image: Abi S.
Verified Enhanced Background Check

11. Abi S.

Star Sitter
I’ll keep up with your pup!
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
30 reviews
12 repeat clients
Profile image

Abi was wonderful!! So respectful of our home and our dog was well loved while we were away!

Availability updated 18 days ago
Sitter Profile Image: Daniel K.
Verified Enhanced Background Check
Sitter Profile Image: Daniel K.
Verified Enhanced Background Check

12. Daniel K.

Pet Care Professional at a Discount
Chicago, IL, 60615
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
Profile image

Daniel was great, he’s very reliable and was flexible when I had to make last minute changes. He also comes across as professional and level headed. My dog seemed to be in good spirits when we got back as well.

Availability updated 9 days ago
Sitter Profile Image: Samantha E.
Verified Background Check
Sitter Profile Image: Samantha E.
Verified Background Check

13. Samantha E.

RoverGO
Professional Pet Sitter & Pup Lover
chicago, IL, 60615
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5.0 out of 5 stars
62 reviews
36 repeat clients
Profile image

Sam did an amazing job watching my dog Josie. Josie is blind and requires help getting around and she can be a little stubborn. Sam was very patient with her and made sure she was very well taken care of. I will definitely book Sam again in the future.

Availability updated 2 days ago
Sitter Profile Image: Karissa L.
Verified Enhanced Background Check
Sitter Profile Image: Karissa L.
Verified Enhanced Background Check

14. Karissa L.

Dog whisperer, walker, and lover
Chicago, IL, 60615
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
15 reviews
6 repeat clients

Karissa loves all animals, especially dogs! She is kind and loving to any furry friend she meets. Hire her and your dog(s) will be in great hands!

Availability updated 11 days ago
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check

15. Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
0.8 mi. away
Boarding, House Sitting, Doggy Day Care
from
$30
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
Profile image

Taylor was a great dog sitter for GiGi! She sent photos and made sure she was well taken care of. I would highly recommend Taylor for any pet sitting services!

Availability updated 3 days ago
Sitter Profile Image: Jasmine P.
Verified Background Check
Sitter Profile Image: Jasmine P.
Verified Background Check

16. Jasmine P.

Rover 101
Star Sitter
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
66 reviews
23 repeat clients
Profile image

Jasmine took excellent care of Zoey while we were out of town for nearly a week. Despite Zoey's nervousness and the challenges it posed initially, Jasmine exercised a lot of patience and willingness to try different things to allow Zoey to feel more safe. And after the first night, Zoey warmed up significantly! Jasmine kept us updated throughout the trip, whether it was the challenges on the first day or the big successes in the days that followed! We really appreciated Jasmine's skills, knowledge, and commitment to taking care of Zoey.

Availability updated 30 days ago
Sitter Profile Image: Roman H.
Verified Enhanced Background Check
Sitter Profile Image: Roman H.
Verified Enhanced Background Check

17. Roman H.

Animal Lover and Cat Owner
Kenwood, Chicago, IL, 60615
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
4 reviews
Profile image

Roman was such a great sitter! Arthur was very comfortable around him. Roman was very thoughtful and caring and made sure to send us photos and videos of Arthur while we were away. Would definitely recommend!

Availability updated 3 days ago
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check

18. Katherine B.

Star Sitter
🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5.0 out of 5 stars
69 reviews
22 repeat clients
Profile image

Simply amazing. We recieved many updates, and came home to a happy and healthy dog and apartment in great condition. Would happily recommend have watch our dog again.

Availability updated 58 days ago
Sitter Profile Image: Masheika S.
Verified Background Check
Sitter Profile Image: Masheika S.
Verified Background Check

19. Masheika S.

Rover 101
All around animal lover 💜🐾
Chicago, IL, 60653
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$100
per night
5.0 out of 5 stars
63 reviews
21 repeat clients
Profile image

Masheika was great! With manolo she is sweet and patient and loves to cuddle him I think she even spoiled him a little bit with all the cuddles :-) I appreciate how flexible she was with the schedule and I will definitely recommend her and will be using her again for Manolo’s needs!

Availability updated 8 days ago
Sitter Profile Image: Karen R.
Verified Enhanced Background Check
Sitter Profile Image: Karen R.
Verified Enhanced Background Check

20. Karen R.

ready to care for your pets!
Chicago, IL, 60615
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
1 review

Wow Karen is great with animals. She is extremely friendly and patient when getting to meet new pets. Karen has two dogs of her own that she takes great care of and loves. I trust Karen with watching my dog Daisy, a pitbull mix, any day as I know Karen will keep Daisy safe and happy. Karen also loves to play with animals! All around she is great with animals and she is very passionate about their care!

Availability updated 21 days ago

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. 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 away
  3. 3. 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

Connect anywhere with the Rover app

Find a loving house sitter in your neighborhood.
Add dates for the most accurate results
Search now