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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.

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.

Restoring Chicago Speakeasy from the 1920s Room 1B
SUPERHOST
Private room · 2 guests · 2 beds · 1 bathroom

Restoring Chicago Speakeasy from the 1920s Room 1BNote: check-in is at noon but you can come as early as you need to pick up the keys and drop off your things. This is a luxurious suite and spa shower room concept. Enter your spa through beautiful French doors. No expense has been spared on this luxurious spa bath that is your own private spa. The spa is supplied with the finest shampoo conditioners lotions Linens towels and bathrobes. Your room number is 1B and your keys will be marked 1B. We are restoring an authentic Chicago Speakeasy from the 1920s study the photographs you'll see we've made great progress. This room is numbered 1B and is up the grand staircase to the second floor accompanying our art gallery. A beautiful and quiet room completely private. Welcome There is an additional $50 per person fee for a third or fourth guest staying in the room.

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

SUPERHOST
  1. Private room
  2. Chicago
Self check in self checkout near downtown Chicago
$48 SGD per night
  1. Entire flat
  2. Chicago
Cabin #102 at 747 Lofts– ADA Accessible!
$106 SGD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Best cozy River West Chicago apartment
$135 SGD per night
SUPERHOST
  1. Entire townhouse
  2. Chicago
Cozy Garden Unit by Downtown & Blue Line Stop
$101 SGD per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Clean, Cozy, Comfortable Studio Near Downtown
$113 SGD per night
SUPERHOST
  1. Entire loft
  2. Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
$143 SGD per night
  1. Entire apartment
  2. Chicago
1 bedroom in historic Gold Coast greystone
$148 SGD per night
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
$96 SGD per night
SUPERHOST
  1. Entire flat
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$138 SGD per night
  1. Entire flat
  2. Chicago
Great Location Studio III
$103 SGD per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$133 SGD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Urban Comfort in the Heart of Chicago
$152 SGD per night

Top-rated things to do in Downtown Chicago

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