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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.

Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOST
Entire loft · 4 guests · 2 beds · 1 bathroom

Lakeview Loft-Vintage Chicago, Modern AmenitiesThe Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

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!!

Holiday rentals for every style

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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

SUPERHOST
  1. Private room
  2. Chicago
Self check in self checkout near downtown Chicago
SUPERHOST
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Cozy Garden Unit by Downtown & Blue Line Stop
SUPERHOST
  1. Entire apartment
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Best cozy River West Chicago apartment
SUPERHOST
  1. Entire guest suite
  2. Chicago
Clean, Cozy, Comfortable Studio Near Downtown
  1. Entire flat
  2. Chicago
New Spot in West Town
  1. Entire apartment
  2. Chicago
1 bedroom in historic Gold Coast greystone
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
SUPERHOST
  1. Entire flat
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from the 1920s Room 1B
  1. Entire flat
  2. Chicago
Cabin #104 at 747 Lofts
SUPERHOST
  1. Entire apartment
  2. Chicago
Urban Comfort in the Heart of Chicago

Top-rated things to do in Downtown Chicago

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