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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.

Modern 1 bdr close to Downtown|West Loop|Restauran
Entire condominium · 4 guests · 1 bed · 1.5 bathrooms

Modern 1 bdr close to Downtown|West Loop|RestauranWonderful new unit located in Chicago's famous Medical District! Enjoy new mattress, comforters, sheets, towels and more! Unit is equipped with Smart TV! High speed internet ensures you remain connected and free of issues. Enjoy use of the kitchen for home cooked meals. Minutes from Downtown, UIC Medical District, Pilsen, West Loop and so much more. Easy access to public transportation, downtown Chicago, i290, West Loop, Taylor St, 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).

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

SUPERHOST
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Catmandu 2
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R1 Private Bedroom in Bridgeport Near Downtown
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  1. Entire guest house
  2. Oak Park
Gallery Loft of Oak Park
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  1. Entire flat
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Spacious, light-drenched studio-private entrance!
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  1. Entire flat
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Ravenswood Manor, Sleeps 4! Close to El and Parks
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  1. Entire loft
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Lakeview Loft-Vintage Chicago, Modern Amenities
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  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
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  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A
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  1. Entire flat
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
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  1. Entire guest house
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Private Studio in Bridgeport, Chicago
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  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
SUPERHOST
  1. Entire flat
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park

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