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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.

  1. Private room
  2. Little Italy
Private Room in GREAT LOCATION to CITY

Private, VERY CLEAN room 5 minutes to downtown with FREE PARKING, GREEN TEA & ALOE memory foam mattress, and an EARLY check-in (11 a.m.). You will have your own door code and may arrive at ANY time and as late as you wish, EASY self check-in guaranteed. I allow LUGGAGE DROP OFF! You can store your luggage in the closet before check-in and after check-out times, you can drop it off and pick it up as early and as late as you would like. The neighborhood is extremely safe even at night :) 


$72 SGD per night
SUPERHOST
  1. Private room
  2. South Chicago
Room H1

Comfortable room in a spacious impeccable house. Kitchen is equipped with all new appliances and utensils. Very quiet and family oriented area. Located next to the intersection of 85th St and commercial Ave. Metra station and bus stop just a couple of blocks away. Lake shore drive and Indiana border just minutes away. Downtown 25 min. Free, safe and abundant parking 24/7.

$33 SGD per night
SUPERHOST
  1. Private room
  2. West Town
Stylish & Charming 1PBR STAYCATION SPACE For You

The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of downtown. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located near the train station giving easy access to other areas of Chicagoland

$119 SGD per night

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Other great holiday rentals in Chicago

  1. Private room
  2. Bridgeport
R1 Prime New House Perfect for your stay
$79 SGD per night
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
$77 SGD per night
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 5
$65 SGD per night
SUPERHOST
  1. Private room
  2. Bridgeport
Bridgeport Art District - Bedroom # 3
$74 SGD per night
  1. Private room
  2. Wicker Park
Convenient location!
$109 SGD per night
  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan
$58 SGD per night
  1. Private room
  2. Maywood
Room 4: The Maywood Manor (Twin Bed, 1 Guest)
$43 SGD per night
  1. Private room
  2. Bridgeport
Private Room A5 by Chinatown
$46 SGD per night
SUPERHOST
  1. Private room
  2. Chinatown
Hotel quality private room near downtown RedLine
$66 SGD per night
  1. Private room
  2. East Rogers Park
Loft Style Private Apt (1 Room- 420 Friendly)
$73 SGD per night
  1. Private room
  2. Bridgeport
Rustic Private BR - 5 min to Chinatown & Downtown
$57 SGD per night
  1. Private room
  2. Woodlawn
Master Bedroom in Spacious and Comfy Chicago Condo
$55 SGD per night