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TrustedHousesitters

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HouseCarers

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House sitting jobs for...

Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Two sweet dogs, one great house, steps to the dog beach!

Sat 20 Dec '25 to Sun 04 Jan '26
(15 nights)
24h
Willowbrook, Illinois, United States Willowbrook, Illinois, United States Visit Website

Dog sitter

Fri 09 Jan '26 to Fri 20 Mar '26
(70 nights)
24h
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Small home in Chicago about 30 minutes from downtown!

Sat 27 Dec '25 to Fri 02 Jan '26
(6 nights)
24h
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Dog Lovers Dream in the Heart of Chicago - Two Sweet Pups Need You

Wed 11 Mar '26 to Sun 15 Mar '26
(4 nights)
24h
Libertyville, Illinois, United States Libertyville, Illinois, United States Visit Website

4 Bedroom 2.5 baths, 6 miles from Lake Michigan & 35 miles from Chicago

Sat 31 Jan '26 to Sun 08 Feb '26
(8 nights)
24h
Libertyville, Illinois, United States Libertyville, Illinois, United States Visit Website

4 Bedroom 2.5 baths, 6 miles from Lake Michigan & 35 miles from Chicago

Sat 28 Feb '26 to Fri 06 Mar '26
(6 nights)
24h
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Lincoln Park neighborhood in a spacious condo and outdoor space

Fri 16 Jan '26 to Mon 19 Jan '26
(3 nights)
24h
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Experienced Bunny sitter in Chicago bungalow for a few days away.

Wed 07 Jan '26 to Sun 11 Jan '26
(4 nights)
24h
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Cat lover needed for two sociable, cuddly calico sisters in Chicago loft/garden

Thu 19 Mar '26 to Thu 26 Mar '26
(7 nights)
1d
Lake Forest, Illinois, United States Lake Forest, Illinois, United States Visit Website

Lake Forest, IL home with Husky :)

Sat 31 Jan '26 to Sat 14 Feb '26
(14 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Quaint St. Charles, Illinois: Only an Hour to Chicago! Quiet Area, Sweet Pets!

Thu 29 Jan '26 to Wed 04 Feb '26
(6 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Friendly Chicago Home with 2 Small Loving Dogs — Seeking Caring Sitters

Thu 12 Feb '26 to Fri 20 Feb '26
(8 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Friendly Chicago Home with 2 Small Loving Dogs — Seeking Caring Sitters

Fri 17 Apr '26 to Tue 21 Apr '26
(4 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Need a sitter - traveling

Wed 24 Dec '25 to Tue 30 Dec '25
(6 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Cozy Logan Square Apartment for the holidays!

Wed 24 Dec '25 to Wed 31 Dec '25
(7 nights)
1d
Springfield, Illinois, United States Springfield, Illinois, United States Visit Website

3 Cat Family

Mon 22 Dec '25 to Mon 29 Dec '25
(7 nights)
1d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Mickey The Labradude

Thu 18 Dec '25 to Mon 22 Dec '25
(4 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Stunning, Spacious and Sunny 2BR Downtown Condo

Fri 26 Dec '25 to Sat 27 Dec '25
(1 night)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Bright and Sunny Condo with a Chill Dog

Fri 16 Jan '26 to Sun 25 Jan '26
(9 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Cozy Uptown apartment with adorable feline companion

Fri 19 Dec '25 to Mon 29 Dec '25
(10 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Large private Chicago home close to downtown with chill dog and cat

Mon 09 Feb '26 to Fri 06 Mar '26
(25 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Chic Chicago Loft for the Holidays with Tito and Cali

Sat 27 Dec '25 to Fri 02 Jan '26
(6 nights)
3d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Chicago coach house, spacious 1 bd 1 ba, 2 cats

Wed 24 Dec '25 to Fri 02 Jan '26
(9 nights)
4d
Chicago, Illinois, United States Chicago, Illinois, United States Visit Website

Cute dogs and apartment in Andersonville

Thu 25 Dec '25 to Tue 30 Dec '25
(5 nights)
5d

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