Chicago vacation rentals

We found 23 vacation rentals in Chicago — enter your dates to book direct

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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.

Last minute specials on Houfy

Harpeth River Farmhouse with a History

Harpeth River Farmhouse with a History

US$272.50
US$330.00 | 25% OFF
Dates: Aug 26 2022 - Aug 27 2022
Cabana Azul

Cabana Azul

US$1937.60
US$2240.00 | 15% OFF
Dates: Aug 26 2022 - Sep 01 2022
Windsor Westside villa 8 BD/6 BA - Sleeps 22

Windsor Westside villa 8 BD/6 BA - Sleeps 22

US$1844.13
US$2305.23 | 25% OFF
Dates: Sep 05 2022 - Sep 10 2022

Featured vacation rentals on Houfy

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Some Beach!  Pet Friendly w/Pool-Hot Tub + More!

Some Beach! Pet Friendly w/Pool-Hot Tub + More!

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Aska Mountain Lodge luxury cabin

Aska Mountain Lodge luxury cabin

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Lazy Bear Chalet

Lazy Bear Chalet

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Blue Moon Lake House  Your Stylish Stay in Fay

Blue Moon Lake House Your Stylish Stay in Fay

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Coastal Breeze Beach Getaway Hilton Head Unit 4409

Coastal Breeze Beach Getaway Hilton Head Unit 4409

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Canaveral 606 brings your soul to the sea & space!

Canaveral 606 brings your soul to the sea & space!

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Anna Maria Island - Azure Bliss Vacation Home

Anna Maria Island - Azure Bliss Vacation Home

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PENTHOUSE OASIS- CANOPY/COFFEE/BREAKFAST/PEACE

PENTHOUSE OASIS- CANOPY/COFFEE/BREAKFAST/PEACE

Most viewed vacation rentals in Chicago

Our guests viewed these book direct rentals the most.

Dorothy's Place

Apartment • Chicago
3 Bedrooms • 1 Bathroom

Cute & Cozy Wicker Park 1-BDRM

Apartment • Chicago
1 Bedroom • 1 Bathroom

Magic Factory Loft Three East

Apartment • Chicago
4 Bedrooms • 4 Bathrooms

Hip Wicker Park Apartment for Long Term Stays!

Apartment • Chicago
2 Bedrooms • 1 Bathroom

Magic Factory Loft Two West

Apartment • Chicago
3 Bedrooms • 2 Bathrooms

Coolest Wicker Park 2-Bedroom

Apartment • Chicago
2 Bedrooms • 1 Bathroom

Magic Factory Loft Two East

Apartment • Chicago
4 Bedrooms • 3 Bathrooms

**New Listing** Lincoln Park Hideaway 1Bed/1Bath

Condo • Chicago
1 Bedroom • 1 Bathroom

Search 23 vacation rentals in Chicago

Search Chicago vacation rentals, houses, condos and more | Houfy on the map

Recommended vacation rentals in Chicago

The Cozy Nest: Beautiful, Quiet, and Safe Condo

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Self check in self checkout near downtown Chicago

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Pet friendly vacation rentals in Chicago

Your Fantastic Futon! 1st Floor TV room with locks

Vacation Home • Chicago
1 Bedroom • 2 Bathrooms

Stylish and Cozy 2BR in Logan Square!

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Historic Lincoln Park Oasis/30+ Day Stays Welcome

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