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300+ places to stay

SUPERHOST
Entire apartment
Rating 4.82 out of 5153 reviews
Huge Top Floor 3 BR Apartment - Free Parking, WiFi
8 guests · 3 bedrooms · 3 beds · 1 bath
Free parking · Wifi · Kitchen · Heating
Price:$59 / night
Entire apartment
Rating 4.71 out of 5147 reviews
Charming Small Minimalist Designer Loft,Blue Line
2 guests · Studio · 1 bed · 1 bath
Wifi · Heating
Price:$50 / night
SUPERHOST
Entire apartment
Rating 4.89 out of 5513 reviews
Basement Studio w/Free St. Parking, Humboldt Park
2 guests · Studio · 2 beds · 1 bath
Wifi · Kitchen · Heating
Price:$45 / night
Entire apartment
Rating 4.79 out of 5114 reviews
Steps to Shops, Eats | Easy Access + W&D | Zencity
5 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Heating
Price:$23 / night
Entire guest suite
Rating 4.64 out of 514 reviews
Bright and Spacious Humboldt Park Master Suite
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Heating
Price:$37 / night
Entire apartment
Rating 4.53 out of 5111 reviews
Steps to Shops, Eats | Open Loft w/ W&D | Zencity
5 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Heating
Price:$23 / night
SUPERHOST
Entire apartment
Rating 4.96 out of 5338 reviews
Great location.
2 guests · 1 bedroom · 1 bed · 1 bath
Free parking · Wifi · Heating
Price:$85 / night
SUPERHOST
Entire condominium
Rating 4.89 out of 5286 reviews
Humboldt Park Traveler's Lodge
3 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Heating
Price:$64 / night
Entire condominium
Rating 4.63 out of 5106 reviews
Entire Top-Floor 2bd/1ba Condo in Wicker Park
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Heating
Price:$54 / night
Plus
Entire apartment
Rating 4.91 out of 577 reviews
Checkerboard Studio with Private Outdoor Hot Tub and Yard
2 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Heating
Price:$59 / night
Entire guest suite
Rating 4.33 out of 53 reviews
Centrally Located Wicker Park Charming Home
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Heating
Price:$35 / night
SUPERHOST
Entire loft
Rating 4.87 out of 5476 reviews
West Town Traveler's Lodge
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Heating
Price:$65 / night
Plus
Entire loft
Rating 4.89 out of 5157 reviews
Urban Chic Loft in Hip Ukrainian Village with Garage
6 guests · 1 bedroom · 1 bed · 1.5 baths
Wifi · Kitchen · Heating
Price:$72 / night
SUPERHOST
Private room
Rating 4.90 out of 569 reviews
The Explorer Room
2 guests · 1 bedroom · 1 bed · 1 shared bath
Wifi · Kitchen · Heating
Price:$50 / night
SUPERHOST
Entire condominium
Rating 4.83 out of 5115 reviews
Best cozy River West Chicago apartment
2 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Heating
Price:$50 / night

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Multi-day trips led by local experts—activities, meals, and stays included
SUPERHOST
Private room
Rating 4.91 out of 5164 reviews
Cozy private room on Chicago's west side
2 guests · 1 bedroom · 0 beds · 1 shared bath
Wifi · Kitchen · Heating
Price:$46 / night
SUPERHOST
Entire condominium
Rating 4.91 out of 575 reviews
▌▌▌THREE LEVEL Skyline View Chicago Penthouse ▌▌▌
14 guests · 3 bedrooms · 3 beds · 2.5 baths
Free parking · Wifi · Kitchen · Heating
Price:$99 / night
SUPERHOST
Entire apartment
Rating 4.64 out of 5370 reviews
Tiny Studio Apartment 94 Walk Score
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Heating
Price:$60 / night
1 18 of 300+ Rentals
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