House Sitting in Kenwood, Chicago

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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1. Emily N.

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

This was the first time we've had someone stay in our home to watch our dog while we were away and Emily was wonderful! She was very attentive to his needs and was able to manage his anxiety meds and special diet. We really appreciated all the photos and detailed updates every day! I would certainly recommend Emily!

Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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2. Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
54 reviews
25 repeat clients
from
$65
per night

Otis did a great job with Bonita, she was happy and healthy after 15 long day away. There was lack of communication but overall I recommend him to take care of your doggy.

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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3. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$65
per night

Crystal responded to my cat sitting request quickly, asked great questions, followed all directions, and my kittens loved her. I will definitely try to book with her in the future!

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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4. Belicia K.

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

Belicia is the absolute best. We were gone for two weeks for our wedding abroad and were so busy that we barely had time to check in the way we normally would. Yet, Belicia made a daily effort to give us the loveliest updates about her time with our girl, giving us total peace of mind.

Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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5. Dalila E.

Rover 101
Star Sitter
PET SPECIALIST
Chicago, IL, 60616
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
85 repeat clients
from
$75
per night

Dalila was excellent with my cat. She send regular updates and very good with communicating. I came back to a happy cat. I will Def be using her services again.

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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6. Saniah I.

Star Sitter
Saniah: Your pets, my love!
Chicago, IL, 60605
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night

Arrived in time and take care of my dog perfectly, great communication all the time, definitely recommend her and super happy with the service provided.

Sitter Profile Image: Juan-Pablo A.
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Sitter Profile Image: Juan-Pablo A.
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7. Juan-Pablo A.

College student and animal lover
Chicago, IL, 60615
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$35
per night

Juan Pablo is great! We had him come sit our rescue dog who gets very anxious when we leave the house. Our dog was completely calm and content, laying close to Juan Pablo, for the entire evening. Juan Pablo is friendly, reliable and compassionate. I will be booking him again!

Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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8. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
15 repeat clients
from
$88
per night

Jonathan took such good care of our dog while we were away! They went on long walks and our dog looked super happy in every picture he sent. Jonathan sent descriptive updates and communicated as needed. We never worried about our pup while we were away. Thanks, Jonathan!

Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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9. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$33
per night

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 ?

Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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10. 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
5.0 out of 5 stars
62 reviews
21 repeat clients
from
$75
per night

Jasmine exceeded our expectations caring for our 3 dogs and 1 cat over the long weekend. She was incredibly communicative, regularly sending updates and photos which put our minds at ease. Our animals seemed happy and well taken care of upon our return. We highly recommend Jasmine for anyone in need of reliable and loving pet care!

Sitter Profile Image: Shakira C.
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Sitter Profile Image: Shakira C.
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11. 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
5.0 out of 5 stars
36 reviews
7 repeat clients
from
$75
per night

This is the second time I’ve asked Shakira to watch my Doberman, Laila and could not be more pleased. My dog can be super energetic and Shakira does a great job with her. I’ve even received compliments from my neighbors of how good she is when I’m away. Shakira is very responsive , detail oriented and sends daily updates and photos. HIGHLY recommend!

Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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12. Nicole C.

Responsible, reliable, WFH 🧘🏻‍♀️
Near South Side, Chicago, IL, 60616
3.0 mi. away
Boarding, House Sitting
5.0 out of 5 stars
15 reviews
1 repeat client
from
$72
per night

Nicole was so great! Updated us with photos of Ernie, took him to the park and made sure he got lots of hangout time. We came back to a clean house and a very happy, relaxed dog. We would definitely use Nicole again!

Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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13. Danielle B.

I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$30
per night

Danielle was great at taking care of my two large dogs. She was very affectionate with my dogs, ensured they got a lot of attention, an brought them on walks where they were able to run freely in the park to get their energy out. Danielle provided me with detailed updates which gave me peace of mind while I was away from my dogs. I would recommend Danielle and would gladly work with her again.

Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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14. Sarah S.

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

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!!

Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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15. Taylor C.

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

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!

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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16. 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
5.0 out of 5 stars
56 reviews
16 repeat clients
from
$75
per night

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.

Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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17. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
5 repeat clients
from
$60
per night

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

Sitter Profile Image: Jonah S.
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Sitter Profile Image: Jonah S.
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18. Jonah S.

Around HP - flexible schedule
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$60
per night

Jonah dog sat Cinnamon and he did a great job with her! I appreciate the daily updates while I was away and that he kept my place tidy. Thank you, Jonah! I will be calling Jonah again in the future.

Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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19. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
1 repeat client
from
$44
per night

I highly recommend Chijioke for pet sitting. They are so reliable and caring!! I have booked them multiple times to pet sit for me while I've been out of town and they do a fantastic job every time! They cleaned the litter, fed and kept my cat company. Chijioke is a great communicator, they are thorough and easy to talk to! Plus they kept me updated throughout! A superstar pet sitter! Highly recommend 10/10!

Sitter Profile Image: Emma & Emily F.
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Sitter Profile Image: Emma & Emily F.
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20. Emma & Emily F.

We love making new furry friends!
Chicago, IL, 60637
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$85
per night

Emma and Emily were wonderful to work with and very communicative while we were away. Our dog and our home were very well cared for. We look forward to working with them again for our next trip!

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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.

House Sitting