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More than 370,000 guests have stayed in Chicago.
On average they rated their stays 4.8 out of 5 stars.

Popular with business travelers

People traveling for work have rated these places highly
SUPERHOST
Entire apartment
Hip Chicago Apartment - FREE Parking Spot Included
4 guests2 bedrooms2 beds1 bath
Free parkingWifiKitchenHeating
Price:$40 / night
Entire apartment
Sonder | Essex on the Park | Desirable 1BR + View
4 guests1 bedroom2 beds1 bath
WifiKitchenHeating
Price:$102 / night
Plus
Entire apartment
Arrive in a Beautiful Loft Style Apartment
8 guests2 bedrooms2 beds2 baths
WifiKitchenHeating
Includes cancellation flexibility
Price:$72 / night
SUPERHOST
Entire condominium
Cozy Apartment with Free Parking
5 guests3 bedrooms3 beds1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$43 / night
Plus
Entire condominium
Uptown/Andersonville Quiet, Charming Condo
4 guests2 bedrooms2 beds2 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$55 / night
Plus
Entire apartment
Archways Apartment Across from Lincoln Park Zoo
5 guests2 bedrooms2 beds2 baths
WifiKitchenHeating
Includes cancellation flexibility
Price:$72 / night
Entire guesthouse
Wicker Shops, Eats, Bars | Outdoor Patio | Zencity
4 guests2 bedrooms2 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$21 / night
Entire apartment
Amazing 2BR-2BA in the heart of Downtown Chicago
10 guests2 bedrooms5 beds2 baths
WifiKitchenHeating
Price:$50 / night
Entire apartment
Lofted 2nd Floor Apartment with Spiral Staircase
5 guests2 bedrooms4 beds1 bath
WifiKitchenHeating
Price:$65 / night
SUPERHOST
Entire loft
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
4 guests2 bedrooms2 beds2 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$89 / night
Entire apartment
⭐️ Charming Two Bedroom Apartment near Downtown ⭐️
5 guests2 bedrooms2 beds1 bath
Free parkingWifiKitchenHeating
Price:$70 / night
SUPERHOST
Entire apartment
❤️ $2000 April Sale! Clean & Stylish 2BR APT
5 guests2 bedrooms2 beds1 bath
Free parkingWifiKitchenHeating
Price:$45 / night
SUPERHOST
Entire condominium
▌▌▌THREE LEVEL Skyline View Chicago Penthouse ▌▌▌
14 guests3 bedrooms4 beds2.5 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$147 / night
Plus
Entire apartment
Eclectic Artist Designed Sanctuary Heart of Pilsen
4 guests2 bedrooms2 beds1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$65 / night
SUPERHOST
Entire apartment
Delightful 3 bed 2 bath with Free Parking!
6 guests3 bedrooms3 beds2 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Price:$67 / night
Plus
Entire apartment
Stunning Retro Apartment in Andersonville
4 guests2 bedrooms2 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$70 / night
SUPERHOST
Entire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
4 guests2 bedrooms2 beds2 baths
Free parkingWifiKitchenHeating
Price:$56 / night
Entire apartment
🏡$2020 DEALS! Homey & Comfy 2BR Near Wrigley
5 guests2 bedrooms3 beds1 bath
WifiKitchenHeating
Price:$45 / night
SUPERHOST
Entire apartment
Stylish 3 Bedroom, Sleeps 6
6 guests3 bedrooms3 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$100 / night
SUPERHOST
Entire townhouse
☆ Modern Spacious Home Free Parking Self CheckIn ☆
8 guests3 bedrooms3 beds1.5 baths
Free parkingWifiKitchenHeating
Price:$80 / night
1 20 of 300+ places to stay
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