Locations

Dates

Responsibilities

Websites

TrustedHousesitters

A 20% discount will be applied automatically using any of our links

HouseCarers

A 10% discount will be applied automatically using any of our links

House sitting jobs for...

Edwardsville, Illinois, United States Edwardsville, Illinois, United States Visit Website

Looking for a cat lover to watch our fur babies while we're away ❤️

Thu 03 Sep '26 to Tue 03 Nov '26
(61 nights)
24h
Indian Head Park, Illinois, United States Indian Head Park, Illinois, United States Visit Website

Sunny, spacious condo in Chicago burbs, caring for two cats. You will need a car

Thu 23 Apr '26 to Wed 13 May '26
(20 nights)
1d
Williamsville, Illinois, United States Williamsville, Illinois, United States Visit Website

Rudy Dood is looking for someone to come hang out with him for a couple of weeks

Wed 15 Apr '26 to Wed 29 Apr '26
(14 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Frida and Romeo are waiting for you in the beautiful city of Chicago.

Sun 12 Apr '26 to Tue 28 Apr '26
(16 nights)
2d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Playful, cuddly lapdog in large vintage home in charming Chicago neighborhood

Fri 08 May '26 to Sat 23 May '26
(15 nights)
2d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Northside Nest in Chicago – Near the Lake (4 blocks), With a Backyard & Pups!

Thu 11 Jun '26 to Wed 24 Jun '26
(13 nights)
2d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Sweet, calm sitter for a good boy right outside of Chicago!

Sun 29 Mar '26 to Sat 04 Apr '26
(6 nights)
2d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Great apartment in Chicago, with a lovely cat.

Sun 21 Jun '26 to Sat 27 Jun '26
(6 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Great apartment in Chicago, with a lovely cat.

Mon 02 Nov '26 to Wed 25 Nov '26
(23 nights)
3d
Rockton, Illinois, United States Rockton, Illinois, United States Visit Website

Bird Haven

Thu 04 Jun '26 to Tue 16 Jun '26
(12 nights)
5d
Batavia, Illinois, United States Batavia, Illinois, United States Visit Website

Historic & charming river town, Batavia IL

Fri 27 Mar '26 to Thu 02 Apr '26
(6 nights)
6d
Oak Brook, Illinois, United States Oak Brook, Illinois, United States Visit Website

Beautiful, and loving rescued King Charles/Border Collie mix in a vibrant area.

Sun 02 Aug '26 to Sun 09 Aug '26
(7 nights)
8d
Oak Brook, Illinois, United States Oak Brook, Illinois, United States Visit Website

Beautiful, and loving rescued King Charles/Border Collie mix in a vibrant area.

Fri 11 Sep '26 to Sun 20 Sep '26
(9 nights)
8d
Oak Brook, Illinois, United States Oak Brook, Illinois, United States Visit Website

Beautiful, and loving rescued King Charles/Border Collie mix in a vibrant area.

Sun 31 Jan '27 to Mon 22 Feb '27
(22 nights)
8d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Sweet and spunky pup in gorgeous South Loop Chicago!

Thu 16 Apr '26 to Mon 20 Apr '26
(4 nights)
9d
Hoffman Estates, Illinois, United States Hoffman Estates, Illinois, United States Visit Website

A cat/house sitter needed for a home in the Chicago NW Sburbs‘s

Thu 02 Apr '26 to Sun 12 Apr '26
(10 nights)
2w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Fetch enthusiasts in NW Chicago oasis

Wed 01 Apr '26 to Sat 11 Apr '26
(10 nights)
2w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Looking for dog babysitter house sitter outside Chicago. Last-minute notice

Sat 11 Apr '26 to Sat 18 Apr '26
(7 nights)
3w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Cat sitter needed in Chicago for 13 days!

Tue 19 May '26 to Sun 31 May '26
(12 nights)
3w
Libertyville, Illinois, United States Libertyville, Illinois, United States Visit Website

Relax & Unwind in North Chicago

Fri 12 Jun '26 to Sat 20 Jun '26
(8 nights)
4w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

2 bedroom with laundry & adorable Westie dog in hip vibrant neighborhood

Fri 03 Apr '26 to Sun 05 Apr '26
(2 nights)
4w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

City Husky Sit

Sat 25 Apr '26 to Tue 05 May '26
(10 nights)
4w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Heart of Chicago with a cuddly cat

Mon 22 Jun '26 to Sun 28 Jun '26
(6 nights)
4w
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Dog Lover’s Dream: House Sit in Roscoe Village with Our King Charles Cavalier

Sat 01 Aug '26 to Sun 09 Aug '26
(8 nights)
4w

© 2026
All Rights Reserved.

Cookie and Privacy Policy

Terms of Use Policy

Affiliate Disclosure: We may receive a small commission (at no cost to you) if you make a purchase after clicking on our links. Find out more.