House Sitting in Kenwood, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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Vladimir C.
Fulltime attention 💛💙 loads of 📸Near North Side, Chicago, IL, 60611
Dog Boarding, House Sitting

Vlad was great with Lucy. He arrived promptly and was very friendly. He took many nice photos of my dog on Michigan avenue. She was happy with him. I recommend … (more)

from
$40
per night
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Susan C.
2.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan was terrific with our two dogs. When we met her prior to her stay, we knew they were in good hands. She sends lots of updates and treats your dogs like th… (more)

from
$60
per night
Confirmed availability: 4th of July
Holly R.
3.
WFH Seasoned SitterWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Holly is truly an exceptional person and dog watcher! We met at a dog park near her house before my dog Jake had his week long stay at her house. And he absolut… (more)

from
$45
per night
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Sarai O.
4.
Reliable, trustworthy & loving!Bridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Sarai is very sweet and Hugo loves her. She sticks to the schedule and cleans everything up before leaving. I highly recommend her. And… Hugo loves her. (more)

from
$80
per night
Confirmed availability: 4th of July
Natalie S.
Parent of Jojo the BorgiNear West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We've used Natalie twice now, and both times have been wonderful! Tater - our 7 year old lab - can be a handful, but he is calm and so happy around Natalie. Tat… (more)

from
$95
per night
Confirmed availability: 4th of July
Your Pup is My PupSouth Shore, Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking

Shakira and Bo had a wonderful time whilst I was off celebrating the marriage of my son with family and friends. I received pics and messages that took the worr… (more)

from
$60
per night
Beloved dog whisperer, is me!South Shore, Chicago, IL, 60649
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jasmine is amazing! She has looked after my Cane Corso a few times now. Her communication is consistent, she gets along great with the pup and he loves her. … (more)

from
$55
per night
Confirmed availability: 4th of July
8.
Pet owner, caregiver, and physicistHyde Park, Hyde Park, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Marvin is a wonderful dog sitter, he is kind and did an amazing job with our pups. He is very on top of caring for our pups and we felt very secure with him in … (more)

from
$45
per night
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Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

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… (more)

from
$75
per night
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10.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emily has stayed in my home with my dogs many times now and she has always done an amazing job. Extremely trustworthy, clean, and my dogs are always well taken … (more)

from
$40
per night
Confirmed availability: 4th of July
11.
🐶 lover from one pet to another!Kenwood, Chicago, IL, 60653
House Sitting, Dog Walking

Dajae was awesome! She left a note for me when I arrived back. She was very kind and communicative throughout the sit. Also, the pics were so cute <3 I will def… (more)

from
$40
per night
12.
Loving care when your not there!!West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Dog Walking

Nataya was wonderful. She took great care of both my cat and dog. She sent daily pictures and videos and was extremely responsive to all of my questions. My pet… (more)

from
$70
per night
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13.
On the move and ready to help!Washington Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking

Great, on time, listened to what was needed and had a happy dog when I got home! Will use her again (more)

from
$30
per night
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14.
Energetic and Focused Pet CareWoodlawn, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking

Becca is a loving, gentle, nurturing pet person. I know for a fact that she grew up in a home with two black labs during her childhood and that she loves both d… (more)

from
$30
per night
15.
Cats and dogs are my sunshine!Englewood, Chicago, IL, 60621
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

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, etc. … (more)

from
$40
per night
Calendar Recently Updated
16.
Dog sitter for hire!Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking
2 years of experience

About: I have had my dog Rory for one year now, and have gained a lot of experience administering medication and dealing with anxiety and reactivity on walk… (more)

from
$30
per night
17.
Walking pets is my favorite hobby!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Grace is wonderful! She’s very trustworthy & caring. I would leave my pet with Grace in a heartbeat & would feel very confident that she would treat them like h… (more)

from
$40
per night
All Creatures, Great and SmallHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

If you need someone who is: 1. Dedicated 2. Loyal 3. A great pet sitter/Lover 4. Flexible with scheduling 5. Local Then Lisa is your Best Choice. She has… (more)

from
$100
per night
Calendar Recently Updated
19.
Consistent & Loving :)Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits

Katlyn was great, coming to meet Blue before our trip. Blue loved her and we felt comfortable leaving her to go on our trip. She was very respectful of our apar… (more)

from
$70
per night
20.
Dogs are four legged best friendsGrand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I love Pamela! She’s an awesome person with a beautiful personality. She’s very kind, sweet, and respectful. She considerate and has the cutest dimples and smil… (more)

from
$55
per night

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.