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Holiday rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Restoring Chicago Speakeasy from 1920's Room 1A
SUPERHOST
Private room · 2 guests · 2 beds · 1 private bathroom

Restoring Chicago Speakeasy from 1920's Room 1ANote : 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

Great location. Free parking.  One night available
SUPERHOST
Entire flat · 2 guests · 1 bed · 1 bathroom

Great location. Free parking. One night availableGreat location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

R7 Suite with Private full Bathroom in Bridgeport
Private room · 2 guests · 1 bed · 1 private bathroom

R7 Suite with Private full Bathroom in BridgeportThis is the best room we can offer to our guests. This fantastic suite comes with a private full bath!!

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Popular amenities for Downtown Chicago holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Downtown Chicago

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Cabin #102 at 747 Lofts– ADA Accessible!
₹5,268 per night
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Cozy Garden Unit by Downtown & Blue Line Stop
₹5,504 per night
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Clean, Cozy, Comfortable Studio Near Downtown
₹6,200 per night
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Lakeview Loft-Vintage Chicago, Modern Amenities
₹7,896 per night
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1 bedroom in historic Gold Coast greystone
₹8,183 per night
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Private Studio in Bridgeport, Chicago
₹5,501 per night
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✨Spacious Centrally Located West Loop Loft✨
₹8,119 per night
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Great Location Studio III
₹5,564 per night
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SHARED Artist Loft . Very Unique
₹7,345 per night
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Urban Comfort in the Heart of Chicago
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