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Over 1,000 places in Chicago

Apartment in Near South Side
Sonder South Wabash | Two-Bedroom Apartment
3 beds
Oct 5 – 10
$640 per night
Hotel in River North
Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe
1 king bed
Oct 17 – 22
$234 per night
Hotel room in Near North Side
Traveler's Dream - 1 bed in a shared bedroom
1 bunk bed
Oct 4 – 9
$120 per night
Apartment in Near North Side
Kasa | Spectacular City Views | Chicago
2 beds
Oct 4 – 9
$456 per night, originally $534
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Oct 8 – 13
$207 per night
Apartment in Near South Side
Sonder South Wabash | Spacious 1BR w/ City View
2 beds
Oct 5 – 10
$408 per night
Superhost
Apartment in Logan Square
Logan Square 2nd Floor Chicago Victorian
2 beds
Oct 26 – 31
$140 per night
Apartment in Near North Side
Kasa | Steps to Oak Street Beach | Chicago
2 beds
Oct 4 – 9
$379 per night, originally $506
Apartment in The Loop
Sonder The Plymouth | Superior 3BR Apt
3 double beds
Oct 9 – 14
$397 per night
Apartment in West Rogers Park
2-Bed, 2-Bath, Brand New apt. Super Clean!
5 beds
Oct 15 – 20
$108 per night
Superhost
Condo in Austin
Clean & Cozy Entire 3 bdrm Unit 7 Miles frm dwntwn
4 beds
Oct 22 – 27
$126 per night
Superhost
Apartment in Logan Square
Lovely Renovated Logan Square 3-bedroom apt
4 beds
Nov 7 – 12
$114 per night
Apartment in River North
Level ◆ New Luxe Two Bedroom Corner Suite
2 beds
Oct 9 – 14
$427 per night
Superhost
Apartment in Austin
Flexible Apt. for 8 by Oak Park-CHI
6 beds
Oct 31 – Nov 5
$163 per night
Condo in Chicago
Cozy Home, mins from McCormick Place/Downtown
3 beds
Oct 15 – 20
$126 per night
Apartment in McKinley Park
Spacious 3 bedroom Apartment
3 beds
Oct 22 – 27
$89 per night
Apartment in Chicago
Relaxing Home mins from McCormick Place/Downtown
2 queen beds
Oct 22 – 27
$113 per night
Superhost
Condo in Woodlawn
Comfy 2 Bedroom Apartment w/ Office
2 beds
Oct 22 – 27
$94 per night