House Sitting in Loop, 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

Calendar Recently Updated
Brandon R.
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
Confirmed availability: Memorial Day
Alison C.
2.
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
Calendar Recently Updated
David N.
3.
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
Calendar Recently Updated
Sharon G.
4.
Dog lover and owner my whole life!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Sharon is very caring and loving person. She loves all animals. She has been taking care of Oscar - yorkie in the most caring way. He is an old dog, so Sharon w… (more)

from
$45
per night
Confirmed availability: Memorial Day
Marjani H.
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
6.
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
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
Confirmed availability: Memorial Day
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
9.
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
Confirmed availability: Memorial Day
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
11.
Lifelong Pet Lover and OwnerLoop, Chicago, IL, 60601
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kailee has been fantastic every time she’s spent time with my two large dogs! I can tell by how excited they get to see her that she takes great care of them an… (more)

from
$45
per night
Calendar Recently Updated
12.
10+ years in pet care experience!Lincoln Park, Chicago, IL, 60614
Dog Boarding, Dog Walking

Addison has watched our Boston Terrier twice now, and we definitely feel that we have found our go to sitter in the city. We feel that our pup gets the attentio… (more)

from
$75
per night
Calendar Recently Updated
Active dog snugglers and walkers!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jess & Drew were absolutely amazing, they watched my dog for me while I was in the hospital recovering from surgery. They were so flexible and understanding, I … (more)

from
$65
per night
Calendar Recently Updated
14.
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
15.
Affordable and Attentive Care!Loop, Chicago, IL, 60603
Dog Boarding

Sabrina was great with my dog and very easy to get in touch with for planning and updates during the stay. My dog loved playing with her puppy while I was away … (more)

from
$45
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
Confirmed availability: Memorial Day
17.
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
18.
21 Year old dog lover!Near South Side, Chicago, IL, 60605
Dog Boarding, Doggy Day Care

Noor watched Zara for a whole week and I felt so comfortable leaving her in Noor’s hands. He sent regular updates and I was able to totally relax during our v… (more)

from
$39
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
20.
Loving retreat for your fur babyNear West Side, Chicago, IL, 60606
Dog Boarding, Doggy Day Care

Anushka is the warmest dog sitter you’ll ever have. I have seen her taken care of her Aussiepom from the past year with outmost love, care and warmth. She has s… (more)

from
$35
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.