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Display total before taxes

Search resultsOver 1,000 places in Chicago

Hotel room in Chicago
Traveler's Dream - 1 bed in a shared bedroom
1 bunk bed
Oct 1 – 6
$42 per night, originally $57
Hotel in Chicago
Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe
1 king bed
Oct 8 – 13
$329 per night
Superhost
Home in Chicago
Luxurious 8 Bed Retreat State of the Art Theater
8 beds
Oct 10 – 15
$632 per night
Boutique hotel in Chicago
Luxury Stay - Claridge House, Queen Room
1 queen bed
Oct 29 – Nov 3
$96 per night
Apartment in Chicago
Sonder Market Hall | Studio Apartment w/ City View
1 king bed
Oct 5 – 10
$356 per night
Apartment in Chicago
Level ◆ New Luxe Two Bedroom Corner Suite
2 beds
Oct 1 – 6
$463 per night
Hotel room in Chicago
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Oct 1 – 6
$170 per night
Apartment in Chicago
Sonder The Plymouth | Superior 3BR Apt
3 double beds
Oct 9 – 14
$355 per night
Superhost
Apartment in Chicago
Logan Square 2nd Floor Chicago Victorian
2 beds
Oct 26 – 31
$140 per night
Apartment in Chicago
Kasa | See the Sites from Your Balcony | Chicago
1 queen bed
Oct 2 – 7
$354 per night, originally $417
Apartment in Chicago
Sonder South Wabash | Two-Bedroom Apartment
3 beds
Oct 5 – 10
$739 per night
Apartment in Chicago
Sonder South Wabash | Studio Apt w/ City View
1 queen bed
Oct 4 – 9
$377 per night
Apartment in Chicago
Kasa | Spectacular City Views | Chicago
2 beds
Oct 2 – 7
$281 per night, originally $410
Apartment in Chicago
Cozy 2 Bedroom
2 beds
Oct 30 – Nov 4
$111 per night
Superhost
Condo in Chicago
Urban Oasis Getaway. 5 stops to downtown
3 beds
Oct 16 – 21
$107 per night
Superhost
Apartment in Forest Park
Walk to Oak Park from a Cozy, Sun-soaked Hideaway
3 beds
Nov 4 – 9
$94 per night
Apartment in Chicago
Sonder The Plymouth | Two-Bedroom Apartment
2 beds
Oct 4 – 9
$474 per night
Superhost
Apartment in Chicago
New and Upscale 3BR Apt with Parking in Lakeview
3 king beds
Oct 20 – 25
$374 per night