Chicago vacation rentals
We found 28 vacation rentals in Chicago — enter your dates to book direct
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Guests
1 guest
Adults
1
Children
0
Pets
Location
Check-in
Check-out
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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
Featured
Charming/Awesome 3 bedroom Home with free parking.
3 Bedrooms 1 Bathroom
Featured
Florida Rentals Near Disney
6 Bedrooms 4.5 Bathrooms
Featured
Immersive Themes* Outdoor Pool & Movie* 5mi Disney
6 Bedrooms 5 Bathrooms
Featured
It’s Always Sunny In Corolla
6 Bedrooms 4 Bathrooms
Featured
5 Sandy Beach Trail
6 Bedrooms 6.5 Bathrooms
Featured
Luxury beach house w/pool, elevator, game room. Steps to Beach
8 Bedrooms 7 Bathrooms
Featured
91 Sandcastle Court
5 Bedrooms 5 Bathrooms
Featured
South Facing Large Villa at Solterra Resort
7 Bedrooms 5.5 Bathrooms
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
Splendid Solterra
10 Bedrooms 10 Bathrooms
$4545.00
$6148.13 | 30% OFF
Dates: Jan 19 2023 - Jan 25 2023
Legacy Lake House
3 Bedrooms 2 Bathrooms
$3193.83
$3954.78 | 40% OFF
Dates: Mar 01 2023 - Mar 31 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
Cosmos Villa
4 Bedrooms 4 Bathrooms
$1811.71
$2231.04 | 20% OFF
Dates: Jan 24 2023 - Feb 05 2023
Large 2 bedroom with Ocean View!! Sleeps 6!
2 Bedrooms 2 Bathrooms
$680.50
$606.00 | 10% OFF
Dates: Jan 10 2023 - Jan 17 2023
Legacy Lake House
3 Bedrooms 2 Bathrooms
$581.21
$657.30 | 15% OFF
Dates: Dec 23 2022 - Dec 26 2022
Most viewed vacation rentals in Chicago
Our guests viewed these book direct rentals the most.
Beautiful home in the heart of Chicago.
Hip Wicker Park Apartment for Long Term Stays!
Magic Factory Loft Three East
Cute & Cozy Wicker Park 1-BDRM
Magic Factory Loft Two West
Whole Home, peaceful and comfy 3 bedrooms
Magic Factory Loft Two East
The Cozy Nest: King Bed in Quiet and Safe Condo
Search 28 vacation rentals in Chicago
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