House Sitters Chicago

freeKim & Jack

We believe that it's important to acknowledge that in the house sitting relationship the owners are affording the sitters the unique privilege of ... View

4 reviews

freeSusan & Bill

We are a retired couple with intentions of traveling all over the country. Bill owned a pet sitting service for several years and managed 30 sitters, ... View

19 reviews

from $19/dayMarion

You want to pick a really trustworthy person to look after your home and your beloved pets (or farm animals). Someone who will never cancel or quit ... View

1 review

freeMohabat & Elina

Hello, I would love to know more about you before I make a commitment, and you can also ask me questions with DM. Thank you.

freeMegan & Zach

Hello! We are Megan & Zach, a married couple in our mid thirties who house sit full time! I am a Teacher at an online elementary school, and Zach ... View

1 review

from $55/dayMaureen

Hello! I am a full time vacation house & pet sitter who enjoys traveling to new places and meeting new people and animals. My passions are animals, ... View

We can not say enough about Maureen, she was just fabulous! She was able to adapt to the many ...... 3 reviews

freeMichelle & James

Hello! Our names are James and Michelle, and we are a married couple who are living in a converted 40ft SKOOLIE (school bus) full time! We both ... View

freeElina

Pets are one of life's greatest joys and it is always my honor to get to meet and love some new animals while their owners are away. I know cat ... View

4 reviews

from $50/dayJerod

Hello! My name is Jerod Foss. I've enjoyed the company of dogs since I was very young. I lived in a very rural area, so most of my time was spent ... View

1 review

freeSkyler & Ashley

Hello! 👋 We are a digital nomad couple and we are seeking house-sitting opportunities. About us: Skyler (30) is originally from Missouri. ... View

freeErin & Eric

As a burnt-out pandemic nurse who is new to working from home, we are looking to reap the benefits of remote work and want to travel and break free ... View

1 review

from $50/dayAnnie

Hi, I'm Annie! I've been moving seasonally for 5 years, and house-sitting regularly for 2 years. I've been a cat lover my whole life, and I ... View

Where do I start?! From the moment we started talking with Annie, I knew I wanted her to be "the ...... 5 reviews

freeRussell & Branwen

A New Zealand/ German artist couple working and traveling around America. We are an artist couple that between artist residencies and exhibitions ... View

freeTorry & Jamie

Coming soon...

freeJeannie & Grant

We’re a couple of joyful, clean and reliable people who take good care of pets and homes that we visit. Remote work allows us to be more mobile and ... View

3 reviews

from $30/dayCarolyn

Greetings homeowners! Your search for a competent, trustworthy and respectful house sitter is over. My name is Carolyn and I'm retired and love to ... View

2 reviews

freeJacqueline & Tracy

We are 2 retired professionals that love to travel and have an extreme love for animals. We have been house sitting since retirement and love it. We ... View

2 reviews

from $75/dayJEFF

Mature, educated, reliable retired professional gentleman available to watch over your home, beloved animals, and farm whenever you must be away. ... View

from $30/dayKatherine

I am a responsible mature, quiet, nonsmoking pet lover. Happy to follow any schedules for your "fur" babies + give them lots of love, & attention. ... View

When the pups are obviously upset that the house sitter is leaving, you know that everything went ...... 25 reviews

freeFred

*****thank you to all the kind and welcoming homeowners and their amazing pets i have had the pleasure of taking care of. Hi. I'm a very young at ... View

Fred was an absolute gem. He looked after our puppy Manchego for two months so wonderfully. He kept ...... 18 reviews