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Vacation rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Catmandu 2
SUPERHOST
Private room · 2 guests · 2 beds · 1 shared bath

Catmandu 2Catmandu bedroom #2: Private room with comfy queen size bed and a loveseat sitting area that pulls out to a single size bed if needed. Bedroom is in close proximity to bath (across the hall).

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

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 apartment · 2 guests · 1 bed · 1 bath

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
  • Wi-Fi
  • 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
$51 NZD per night
  1. Entire condominium
  2. Chicago
Modern 1 bdr close to Downtown|West Loop|Restauran
$112 NZD per night
SUPERHOST
  1. Entire guesthouse
  2. Oak Park
Gallery Loft of Oak Park
$158 NZD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious, light-drenched studio-private entrance!
$116 NZD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$118 NZD per night
SUPERHOST
  1. Entire loft
  2. Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
$149 NZD per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
$105 NZD per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
$56 NZD per night
SUPERHOST
  1. Entire serviced apartment
  2. Chicago
PRIVATE 2-bedroom 1.5 bath w/ living room
$111 NZD per night
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Private Studio in Bridgeport, Chicago
$100 NZD per night
  1. Entire guest suite
  2. Chicago
Modern Chicago Bungalow Guest Suite
$112 NZD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
$81 NZD per night

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