Chicago vacation rentals
We found 28 vacation rentals in Chicago — enter your dates to book direct
Location
Check-in
Check-out
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Guests
1 guest
Adults
1
Children
0
Pets
Location
Check-in
Check-out
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Guests
1 guest
Adults
1
Children
0
Pets
Book direct on Houfy and find a vacation rental that matches your expectations among all these great properties in Chicago. Each of the accommodations are being offered directly by owners and managers. Book direct and save up to 25% in commissions and service fees only on Houfy.
Featured vacation rentals on Houfy
Last minute specials on Houfy

A & R Hacienda - In the Heart of Callicoon, NY
3 Bedrooms 2 Bathrooms
$1039.50
$1260.00 | 20% OFF
Dates: Feb 17 2023 - Feb 20 2023

Paradise at the Smokies Cabin
3 Bedrooms 1 Bathroom
$975.51
$1068.87 | 10% OFF
Dates: Jan 16 2023 - Jan 22 2023

Beautiful home in the heart of Chicago.
4 Bedrooms 3 Bathrooms
$1815.00
$2130.00 | 15% OFF
Dates: Jan 05 2023 - Jan 11 2023
Most viewed vacation rentals in Chicago
Our guests viewed these book direct rentals the most.
Search 28 vacation rentals in Chicago
Search Chicago vacation rentals, houses, condos and more | Houfy on the map