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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
SHARED Artist Loft . Very Unique
SUPERHOST
Private room · 3 guests · 1 bed · 1 private bathroom
SHARED Artist Loft . Very UniqueNote: Check-in is at noon but you can come earlier pick up the keys and drop off your bags. NOTE: If the date your looking for is not available i have another beautiful room listed as, Artist Loft own private room. Look for it. Thank you. A BRIGHT airy loft bedroom with curtains for privacy, A beautiful room to wake up in. Flowered outdoor deck in the middle of famous River North Chicago is a wonderful start to enjoying everything this great city has to offer. This neighborhood is rocking on weekends. If a super light sleeper this room is not for you on weekends check my other listing. There is a $50 fee per person for the third and fourth person staying in the room.
Great location. Free parking.
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Great location. Free parking.Great 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.

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Popular amenities for Downtown Chicago holiday rentals

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

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Lincoln Park Avant Artist's Private 1891 Apartment
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The Lakefront Lookout (2BR)
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Beautifully Renovated, Walking distance to Lake!
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Get Cozy at a Powder-Blue Residence in the Heart of Pilsen