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Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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

Gorgeous, cozy 1-bedroom Suite in Andersonville
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bathroom
Gorgeous, cozy 1-bedroom Suite in AndersonvilleOur place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, the location and of course, complete privacy. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.
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.
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

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Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

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Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOST
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Lux 1 bdr in Ravenswood,close to Wrigley|Downtown
SUPERHOST
  1. Entire guest house
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Private Coach house near Lincoln Square!
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
SUPERHOST
  1. Entire rental unit
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Luxurious Top Floor Apartment
  1. Entire rental unit
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Lovely Studio in Great Location Chicago
SUPERHOST
  1. Entire rental unit
  2. Chicago
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy loft in Chicago's Uptown near CTA/Red Line
SUPERHOST
  1. Private room
  2. Chicago
m5- Self check in near downtown Chicago
PLUS
  1. Entire rental unit
  2. Chicago
Redesigned Lower Level Studio in Historic Building
  1. Private room
  2. Chicago
Charming Basement with Private Bath- Sleeps 2