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Over 370,000 guest reviews for places to stay in Chicago, with an average of 4.8 out of 5 stars.

23 places to stay

SUPERHOST
Private room
Rating 4.74 out of 546 reviews
Little Farm in the City
1 guest · 1 bedroom · 1 bed · 1.5 shared baths
Wifi · Kitchen · Heating
Private room
Rating 4.54 out of 528 reviews
Cozy and charming home in Beverly
2 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Kitchen · Heating
Castle
Rating 4.78 out of 5132 reviews
The Castle on Berwyn
4 guests · 2 bedrooms · 2 beds · 1 bath
Free parking · Wifi · Kitchen · Heating
SUPERHOST
Tiny house
Rating 4.69 out of 526 reviews
Cozy Wicker Park home - walk to blue line!
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Heating
Private room
Rating 4.33 out of 512 reviews
Tiny Room.The Cubs Area. Boyztown.ParkingPermitsAv
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Heating
Private room
Rating 5.0 out of 53 reviews
Cozy Tiny Home
2 guests · 1 bedroom · 1 bed · 1 shared bath
Wifi · Kitchen · Heating
Camper/RV
Rating 4.81 out of 564 reviews
Tiny House Camper in the City
2 guests · 1 bedroom · 1 bed · 1 bath
Free parking · Wifi · Kitchen · Heating
Shared room
Rating 5.0 out of 53 reviews
Pillow Top Queen Size 2
2 guests · 1 bedroom · 1 bed · 1.5 shared baths
Wifi · Kitchen · Heating
Barn
Rating 5.0 out of 54 reviews
Beautiful, bright, art-filled loft.
4 guests · 2 bedrooms · 2 beds · 2 baths
Wifi · Kitchen · Heating
Boat
The Hideout
3 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Heating
SUPERHOST
Boat
Rating 4.85 out of 552 reviews
Cozy sailboat in urban harbor
4 guests · Studio · 3 beds · Half-bath
Wifi
Private room
Rating 5.0 out of 54 reviews
Castle-like, Revival Tudor, International Mansion
4 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Heating
SUPERHOST
Castle
Rating 4.85 out of 548 reviews
LOFT606: Gigantic Sunlit Loft!
16+ guests · 6 bedrooms · 9 beds · 2.5 baths
Free parking · Wifi · Kitchen · Heating
Boat
Sleep in LUXURY BOAT + optional private river tour
4 guests · 2 bedrooms · 3 beds · 2 baths
Kitchen · Heating
Campsite
Rating 5.0 out of 59 reviews
Chicago rooftop
4 guests · Studio · 0 beds · Half-bath
Wifi
Private room
Castle-like, Revival Tudor, International Mansion
2 guests · 1 bedroom · 1 bed · 1 shared bath
Wifi · Heating
Camper/RV
Brand New Camper in St Petersburg FL
4 guests · Studio · 2 beds · 1 bath
Free parking · Kitchen · Heating
Shared room
Queen Size Pillow Top 1
2 guests · 1 bedroom · 1 bed · 2 shared baths
Wifi · Kitchen · Heating
1 18 of 23 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.