House Sitting In Near West Side 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

Confirmed availability: Memorial Day
Kimberly M.
Animal lover!park nearby/work at🏠Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Dog Walking

This was my first time boarding my 2 dogs with Kimberly. Kimberly did an excellent job keeping me informed and sending pictures/videos. If you need your pet tak… (more)

from
$44
per night
Calendar Recently Updated
David N.
2.
NOT JUST A PET BUT FAMILYLower West Side, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

David is GREAT! As soon as we get close to his house, Richie starts getting excited and tries to get to David as soon as he sees him! I really love that Richie … (more)

from
$40
per night
Confirmed availability: Memorial Day
Alexandra S.
Dog whispererNorth Center, Chicago, IL, 60618
Dog Boarding, Doggy Day Care

Bithia would send multiple videos and pictures with out even needing to request. She helped me over thanksgiving while on vacation for a much needed break. I… (more)

from
$48
per night
Calendar Recently Updated
Jaclyn N.
4.
Dogs are my favorite people!Near West Side, CHICAGO, IL, 60608
Dog Boarding

Jackie took care of our Maltese, Lychee, whenever I had to travel for work or for a family vacation. Jackie is detail-oriented and sends regular updates with pi… (more)

from
$35
per night
Confirmed availability: Memorial Day
Grace A.
5.
Here for you and your fur-babyWest Town, Chicago, IL, 60642
Dog Boarding, Doggy Day Care

Honestly just the best, I am so thankful for Grace and how she treated Juju! Not only do I recommend her but also hope she’s available all the times I need caus… (more)

from
$50
per night
Calendar Recently Updated
Vet tech, animal loverWest Town, Chicago, IL, 60642
Dog Boarding

I’ve known Margaret as a friend and coworker for the last 3 years. We worked together as veterinary technicians for a small animal practice in Chicago. She is s… (more)

from
$50
per night
Calendar Recently Updated
7.
Playtime Pawtastic!North Side, Chicago, IL, 60647
Dog Boarding, Doggy Day Care

Dana is the best! I have used her a few times before, and always look for her availability. She treats your dog as her own and is very responsive and sweet. She… (more)

from
$60
per night
Confirmed availability: Memorial Day
WORK FROM HOME, Dog Fun House!!Near West Side, Chicago, IL, 60612
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Whitney and her family were fantastic! They took great care of Leela. Leela loved all the attention, play and care but most of all loved playing with their ador… (more)

from
$48
per night
Calendar Recently Updated
Loving home away from homeNear West Side, Chicago, IL, 60607
Dog Boarding

Ryan and Lai took excellent care of my dog while I was away for two days. I felt they loved my dog from the time of meet and greet. I was at peace that my dog w… (more)

from
$45
per night
Calendar Recently Updated
10.
Couple working from 🏡. Free bath!Lower West Side, Chicago, IL, 60608
Dog Boarding

We were gone a week and they sent daily photos and videos of our pup! Communication was excellent and they took great care of our dog. Would highly recommend. (more)

from
$54
per night
Confirmed availability: Memorial Day
11.
Alll breeds and sizes welcomed!Near West Side, Chicago, IL, 60612
Dog Boarding, Doggy Day Care

Megan took care of our 40 lb, 6 year old goldendoodle for 10 days at her house. It was clear that she cared for & loved our dog. It was over Christmas, and she … (more)

from
$50
per night
Calendar Recently Updated
12.
A Dawg who loves Dogs!Near North Side, Chicago, IL, 60654
Dog Boarding, Doggy Day Care

Frida was so happy and comfortable with Alona and Max!! Thank you ? (more)

from
$45
per night
Calendar Recently Updated
Dog lovers looking for dogs in lifeWest Town, Chicago, IL, 60642
Dog Boarding

Bridget and Nick took great care of our Bernie while we were gone for two nights. She felt so completely comfortable that she trotted up the stairs, made hersel… (more)

from
$49
per night
Calendar Recently Updated
14.
Work from home/flexible pet sitter!Near North Side, Chicago, IL, 60654
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Aurora had a blast with Brandon! His dog Macintosh is a total sweetheart and they quickly became friends. They spent a lot of time at dog parks and long walks a… (more)

from
$55
per night
Calendar Recently Updated
WFH dog mom ready to spoil your pupWest Town, Chicago, IL, 60642
Dog Boarding

Adrienne is a caring, responsible, and attentive dog mom who will go above and beyond in taking care of your dog. She has watched my dog in the past, and I knew… (more)

from
$55
per night
Confirmed availability: Memorial Day
16.
Your pups new favorite Auntie!Near South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

Our dogs loved Marjani — so much they seem sad to be back with us! ? Marjani sent daily updates and even to take time to add details that I always miss when I’m… (more)

from
$60
per night
Calendar Recently Updated
17.
Caring and friendly dog-momWest Town, Chicago, IL, 60622
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

We left Ozzie with Kaitlin for a long weekend out of town and she took great care of him. It was such a relief to know that he was in a loving home and receivin… (more)

from
$55
per night
Confirmed availability: Memorial Day
18.
I will love your pet like my own.Near West Side, Chicago, IL, 60661
Dog Boarding, Doggy Day Care

Very good experience with Zarina! She sent us pictures as soon as Pasta was settled in and then kept us updated throughout the weekend! We will definitely come … (more)

from
$50
per night
Calendar Recently Updated
19.
Amy 
Verified Enhanced Background Check
Enthusiastic Dog AdorerLoop, Chicago, IL, 60604
Dog Boarding, House Sitting, Doggy Day Care

Amy did a great job of looking after Hershey on short notice. She was very communicative and thoughtful in all of our interactions. She sent pictures and videos… (more)

from
$50
per night
Confirmed availability: Memorial Day
20.
Work from home | Treats. Play. ♥️Loop, Chicago, IL, 60607
Dog Boarding

Alison is a life saver! I am currently in the process of moving and she has been nothing but an Angel when it comes to taking care of my baby Koda. I can tell h… (more)

from
$80
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.