Skip to content
300+ stays

Stays in Downtown Chicago

Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
SUPERHOST
Entire loft in Chicago
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
4 guests2 bedrooms2 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.91 out of 5;490 reviews
Price:$141 / night
SUPERHOST
Entire condominium in Chicago
▌▌▌THREE LEVEL Skyline View Chicago Penthouse ▌▌▌
14 guests3 bedrooms4 beds2.5 baths
Free parkingWifiAir conditioningKitchen
Rating 4.82 out of 5;102 reviews
Price:$175 / night
SUPERHOST
Entire house in Chicago
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
10 guests3 bedrooms4 beds2.5 baths
Free parkingWifiAir conditioningKitchen
Rating 4.99 out of 5;158 reviews
Price:$599 / night
SUPERHOST
Entire apartment in Chicago
Zen Loft Downtown Chicago
10 guests4 bedrooms5 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.87 out of 5;60 reviews
Price:$643 / night
SUPERHOST
Entire apartment in Chicago
Great location.
2 guests1 bedroom1 bed1 bath
Free parkingWifiAir conditioning
Rating 4.96 out of 5;413 reviews
Price:$88 / night
Entire apartment in Chicago
No crazy fees! Instant Book it! Great Location!
8 guests2 bedrooms5 beds1 bath
Free parkingWifiAir conditioningKitchen
Rating 4.69 out of 5;220 reviews
Price:$73 / night
PLUS
Entire apartment in Chicago
Eclectic Artist Designed Sanctuary Heart of Pilsen
4 guests2 bedrooms2 beds1 bath
Free parkingWifiAir conditioningKitchen
Rating 4.86 out of 5;236 reviews
Price:$125 / night
PLUS
Entire apartment in Chicago
River North's Rock N Roll - Covd Safer, No Common Areas
6 guests2 bedrooms2 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.90 out of 5;145 reviews
Price:$300 / night
SUPERHOST
Private room in Chicago
Private bed/bathroom in East Lakeview/Wrigleyville
2 guests1 bedroom1 bed1 private bath
Free parkingWifiAir conditioningKitchen
Rating 4.96 out of 5;276 reviews
Price:$71 / night
PLUS
Entire condominium in Chicago
Chic and Charming Vintage Condominium in Lincoln Park
6 guests3 bedrooms6 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.80 out of 5;121 reviews
Price:$144 / night
SUPERHOST
Entire apartment in Chicago
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
6 guests2 bedrooms4 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.86 out of 5;57 reviews
Price:$180 / night
SUPERHOST
Entire apartment in Chicago
Fully Furnished Apartment Wicker Park Free Parking
2 guests1 bedroom1 bed1 bath
Free parkingWifiAir conditioningKitchen
Rating 4.98 out of 5;216 reviews
Price:$98 / night
PLUS
Entire loft in Chicago
Be Inspired in a Modernist, Creative, Light-Filled Loft
4 guests2 bedrooms2 beds1 bath
Free parkingWifiAir conditioningKitchen
Rating 4.96 out of 5;78 reviews
Price:$116 / night
SUPERHOST
Entire apartment in Chicago
Lincoln Park Private Garden Suite—free parking
3 guests1 bedroom2 beds1 bath
Free parkingWifiAir conditioning
Rating 4.83 out of 5;236 reviews
Price:$65 / night
PLUS
Entire apartment in Chicago
Trendy West Loop Brownstone with Front Garden
4 guests1 bedroom1 bed1 bath
Free parkingWifiAir conditioningKitchen
Rating 4.98 out of 5;136 reviews
Price:$110 / night
SUPERHOST
Entire apartment in Chicago
River North's Finest - Covid Safer - Monthly Only
6 guests2 bedrooms2 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.82 out of 5;188 reviews
Price:$132 / night
SUPERHOST
Entire apartment in Chicago
Peaceful River West Apt - free gated parking
4 guests2 bedrooms2 beds1 bath
Free parkingWifiAir conditioningKitchen
Rating 5.0 out of 5;119 reviews
Price:$176 / night
SUPERHOST
Entire apartment in Chicago
Kasa | Chicago | Classy 2BD/2BA South Loop Apartment
6 guests2 bedrooms3 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.86 out of 5;35 reviews
Price:$242 / night
SUPERHOST
Entire apartment in Chicago
▶Lofty 3Bd Apt Next to McCormick✔Downtown✔Wintrust
5 guests3 bedrooms5 beds2 baths
Free parkingWifiAir conditioningKitchen
Rating 4.97 out of 5;67 reviews
Price:$234 / night
SUPERHOST
Entire apartment in Chicago
Garden Apartment in the Historic Heart of the City
4 guests1 bedroom1 bed1 bath
Free parkingWifiKitchen
Rating 4.78 out of 5;80 reviews
Price:$85 / night
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.