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Vacation 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 · 2 beds · 1 private bath

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge 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 Also has an Amazon Firestick and 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.

Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guesthouse · 3 guests · 1 bed · 1 bath

Private Studio in Bridgeport, ChicagoA bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

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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. Chicago
Cozy Chicago Hideaway
$82 AUD per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
$47 AUD per night
$47.00 AUD total
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$53 AUD per night
$53.00 AUD total
SUPERHOST
  1. Entire guest suite
  2. Chicago
Private Suite w/ offstreet pkg, at Logan Sq Blu Ln
$56 AUD per night
$56.00 AUD total
SUPERHOST
  1. Entire loft
  2. Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
$138 AUD per night
$138.00 AUD total
SUPERHOST
  1. Private room
  2. Chicago
Lincoln Square In-laws Suite: Private Entrance
$76 AUD per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
$97 AUD per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ukrainian Village Garden Retreat
$122 AUD per night
$122.00 AUD total
SUPERHOST
  1. Entire apartment
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
$75 AUD per night
$75.00 AUD total
SUPERHOST
  1. Private room
  2. Hickory Hills
Private Lower level suite w/ private garage access
$65 AUD per night
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Boutique Guest House in Logan Square w/ King Bed
$113 AUD per night
$113.00 AUD total
  1. Entire apartment
  2. Chicago
Cool and Comfy First Floor in hoppin' Logan Square
$110 AUD per night
$110.00 AUD total

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