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
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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.

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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.

Charming/Awesome 3 bedroom Home with free parking.

Featured
Florida Rentals Near Disney

Florida Rentals Near Disney

Featured
Immersive Themes* Outdoor Pool & Movie* 5mi Disney

Immersive Themes* Outdoor Pool & Movie* 5mi Disney

Featured
It’s Always Sunny In Corolla

It’s Always Sunny In Corolla

Featured
5 Sandy Beach Trail

5 Sandy Beach Trail

Featured
Luxury beach house w/pool, elevator, game room. Steps to Beach

Luxury beach house w/pool, elevator, game room. Steps to Beach

Featured
91 Sandcastle Court

91 Sandcastle Court

Featured
South Facing Large Villa at Solterra Resort

South Facing Large Villa at Solterra Resort

Last minute specials on Houfy

A & R Hacienda - In the Heart of Callicoon, NY

A & R Hacienda - In the Heart of Callicoon, NY

$1039.50
$1260.00 | 20% OFF
Dates: Feb 17 2023 - Feb 20 2023
Splendid Solterra

Splendid Solterra

$4545.00
$6148.13 | 30% OFF
Dates: Jan 19 2023 - Jan 25 2023
Legacy Lake House

Legacy Lake House

$3193.83
$3954.78 | 40% OFF
Dates: Mar 01 2023 - Mar 31 2023
Paradise at the Smokies Cabin

Paradise at the Smokies Cabin

$975.51
$1068.87 | 10% OFF
Dates: Jan 16 2023 - Jan 22 2023
Beautiful home in the heart of Chicago.

Beautiful home in the heart of Chicago.

$1815.00
$2130.00 | 15% OFF
Dates: Jan 05 2023 - Jan 11 2023
Cosmos Villa

Cosmos Villa

$1811.71
$2231.04 | 20% OFF
Dates: Jan 24 2023 - Feb 05 2023
Large 2 bedroom with Ocean View!! Sleeps 6!

Large 2 bedroom with Ocean View!! Sleeps 6!

$680.50
$606.00 | 10% OFF
Dates: Jan 10 2023 - Jan 17 2023
Legacy Lake House

Legacy Lake House

$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.

Beautiful home in the heart of Chicago.

Vacation Home • Chicago
4 Bedrooms • 3 Bathrooms
Hip Wicker Park Apartment for Long Term Stays!

Hip Wicker Park Apartment for Long Term Stays!

Apartment • Chicago
2 Bedrooms • 1 Bathroom
Magic Factory Loft Three East

Magic Factory Loft Three East

Apartment • Chicago
4 Bedrooms • 4 Bathrooms
Cute & Cozy Wicker Park 1-BDRM

Cute & Cozy Wicker Park 1-BDRM

Apartment • Chicago
1 Bedroom • 1 Bathroom
Magic Factory Loft Two West

Magic Factory Loft Two West

Apartment • Chicago
3 Bedrooms • 2 Bathrooms
Whole Home, peaceful and comfy 3 bedrooms

Whole Home, peaceful and comfy 3 bedrooms

Vacation Home • Park Forest
3 Bedrooms • 1 Bathroom
Magic Factory Loft Two East

Magic Factory Loft Two East

Apartment • Chicago
4 Bedrooms • 3 Bathrooms
The Cozy Nest: King Bed in Quiet and Safe Condo

The Cozy Nest: King Bed in Quiet and Safe Condo

Condo • Chicago
3 Bedrooms • 2 Bathrooms

Search 28 vacation rentals in Chicago

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

Recommended vacation rentals in Chicago

2bdr apartment +free parking near train in Chicago

2bdr apartment +free parking near train in Chicago

Apartment • Chicago
2 Bedrooms • 1 Bathroom
Historic Lincoln Park Oasis/30+ Day Stays Welcome

Historic Lincoln Park Oasis/30+ Day Stays Welcome

Condo • Chicago
4 Bedrooms • 2 Bathrooms
Work Or Visiting Place To Stay, O'Hare/Rosemont...

Work Or Visiting Place To Stay, O'Hare/Rosemont...

Condo • Harwood Heights
1 Bedroom • 1 Bathroom
Millennium Park 2 bedroom & 2 Bathroom Condo

Millennium Park 2 bedroom & 2 Bathroom Condo

Condo • Chicago
2 Bedrooms • 2 Bathrooms
Elegant Four-Level Plush Home

Elegant Four-Level Plush Home

Vacation Home • Chicago
6 Bedrooms • 4 Bathrooms
Modern Spacious 4/BDR Private Parking/Wifi,Netflix

Modern Spacious 4/BDR Private Parking/Wifi,Netflix

Apartment • Chicago
4 Bedrooms • 1 Bathroom
Self check in self checkout near downtown Chicago

Self check in self checkout near downtown Chicago

Vacation Home • Chicago
1 Bedroom • 2 Bathrooms
Cozy guest room 1 block from U of C

Cozy guest room 1 block from U of C

Apartment • Chicago
1 Bedroom • 1 Bathroom

Vacation houses with pools in Chicago

Lovely Apartment Downtown Chicago

Lovely Apartment Downtown Chicago

Apartment • Chicago
1 Bedroom • 1 Bathroom

Pet friendly vacation rentals in Chicago

Luxury King Sleep Number - Historic Safe Location

Luxury King Sleep Number - Historic Safe Location

Condo • Elmwood Park
2 Bedrooms • 1 Bathroom
90s Condo- Safe Family Friendly- Arcade Game!

90s Condo- Safe Family Friendly- Arcade Game!

Condo • Elmwood Park
2 Bedrooms • 1 Bathroom
Safe Modern 2BrCondo City Access

Safe Modern 2BrCondo City Access

Apartment • Elmwood Park
2 Bedrooms • 1 Bathroom
Your Fantastic Futon! 1st Floor TV room with locks

Your Fantastic Futon! 1st Floor TV room with locks

Vacation Home • Chicago
1 Bedroom • 2 Bathrooms