Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A

Note : Check in is at noon but you can come as early as you need pick up the keys and drop off your things. Welcome to an Authentic Chicago Speakeasy from the 1920s. Your room is numbered 1A and your keys will be marked 1A. We are currently restoring this original Speakeasy from the 1920s to its former glory. There is an additional $50 fee per person for the third and fourth guests staying in the room. PLEASE NOTE:::: We are cleaning painting and doing light construction during the day here in the common areas. Please be advised. Please read the complete summary before you book. It is not fair for anyone to be given a bad review because someone didn't read the summary of what they were booking. Thank you for understanding this. Your bedroom is completely restored. and the main bath is totally adequate for your needs. Some work will be going on during the daytime in the common areas. No work is done after 6:00 in the evening. Feel free to walk throughout the two floors and observe the restoration process. I am an artist for over 40 years and will be opening M gallery on the second floor. It will be an art gallery and event space hosting art exhibits and concerts. We are loving this grand space and the process of restoring it. Come join us. michaelmccafrey.com

$105 per night
  1. Private room
  2. Chicago
Stunning downtown High Rise apartment amazing view

This newly renovated apartment building offers you everything you could dream of including an amazing view of the Iconic Chicago skyline through the it’s floor to ceiling windows. This unit specifically has a clean modern loft aesthetic.

$97 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #207 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

$72 per night

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Other great vacation rentals in Downtown Chicago

SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★ The Blue Room
$77 per night
  1. Entire rental unit
  2. Chicago
New Spot in West Town
$86 per night
SUPERHOST
  1. Private room
  2. Chicago
Hotel quality private room near downtown RedLine
$46 per night
  1. Entire rental unit
  2. Chicago
1 Bedroom Apartment by McCormick Place & Chinatown
$61 per night
SUPERHOST
  1. Entire home
  2. Chicago
Free parking, close to public transit, dining
$75 per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago speakeasy of the 1920s. Room 4A
$100 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #206 at 747 Lofts
$65 per night
SUPERHOST
  1. Private room
  2. Chicago
Shared Artist Loft Own Private Room
$108 per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★ The Garden Room
$76 per night
  1. Entire rental unit
  2. Chicago
Cute Designer Touch Minimal Loft,Blue Line
$83 per night
SUPERHOST
  1. Entire condo
  2. Chicago
GLORIOUS GOLD COAST GETAWAY
$85 per night
  1. Entire rental unit
  2. Chicago
Modern Floor to Ceiling 1 BDRM - City/Lake Views
$191 per night