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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.

Casa de Sueño/Private Bathroom/Near Train/Loyola
Private room · 2 guests · 1 bed · 1 private bathroom

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge, portable AC IN BR, Blackout curtains, flat screen TV with Apple TV with free Netflix, you can Stream movies/shows through your Apple device or use one of these converter apps to stream from android: https://letsview.com/mirror-android-to-apple-tv.html HDMI hookup. Iron/board, closet w/ hangers, sharper image radio/speakers/cd player, basic office supplies. Printer in LR. Free parking with permits (ask).

Cozy guest room 1 block from U of C
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bathroom

Cozy guest room 1 block from U of CCozy guest room with office desk and futon. Kitchen and living room are available for guest(s) to use. 1 block from University of Chicago, 15 minutes from downtown, 2 blocks from Metra, 4 blocks from Lake Shore Drive and CTA Green Line train. Nearby historic Hyde Park area. Grocery store Jewel-Osco is within walking distance. Parking is street parking 1/2 block away from the apartment. Host lives at listing.

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.

Holiday rentals for every style

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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

  1. Entire guest suite
  2. Berwyn
3rd Floor Private Suite close to Chicago Loop
$71 SGD per night
PLUS
  1. Entire flat
  2. Chicago
Stunning Retro Apartment in Andersonville
$124 SGD per night
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  1. Private room
  2. Willow Springs
Catmandu 2
$57 SGD per night
  1. Private room
  2. Chicago
R1 Private Bedroom in Bridgeport Near Downtown
$56 SGD per night
  1. Entire condominium
  2. Chicago
Modern 1 bdr close to Downtown|West Loop|Restauran
$108 SGD per night
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  1. Entire flat
  2. Chicago
Spacious, light-drenched studio-private entrance!
$112 SGD per night
SUPERHOST
  1. Entire flat
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$113 SGD per night
SUPERHOST
  1. Entire flat
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$120 SGD per night
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
$100 SGD per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
$40 SGD per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from the 1920s Room 1B
$135 SGD per night
SUPERHOST
  1. Entire flat
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
$78 SGD per night

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