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Vacation rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

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

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.
Restoring Chicago speakeasy of the 1920s room 3A
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
Restoring Chicago speakeasy of the 1920s room 3AIf you are having trouble booking a night call me. Michael: 3124515213 My son Todd and I are currently restoring a gem from Chicago's history. we have made great progress in the last year and now our down to simple painting touch-ups Come be part of it. M&T
Polk Street Coach House Apartment, Little Italy/Medical Dist
PLUS
Entire guesthouse · 6 guests · 2 beds · 1 bath
Polk Street Coach House Apartment, Little Italy/Medical DistCook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs.

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Other great holiday rentals in Downtown Chicago

SUPERHOST
  1. Entire townhouse
  2. Chicago
Cozy Garden Unit by Downtown & Blue Line Stop
$99 NZD per night
PLUS
  1. Entire rental unit
  2. Chicago
Trendy West Loop Brownstone with Front Garden
$133 NZD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
$127 NZD per night
PLUS
  1. Entire rental unit
  2. Chicago
Urban Chic Apartment by the Magnificent Mile
$341 NZD per night
  1. Entire rental unit
  2. Chicago
The Executive's Escape (2BR)
$324 NZD per night
PLUS
  1. Entire loft
  2. Chicago
Pilsen Modernist, Creative, Lightfilled Loft
$167 NZD per night
SUPERHOST
  1. Private room
  2. Chicago
🌟 Cozy Bedroom by Downtown & Train; Rooftop Deck!🌟
$60 NZD per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★ Interactive Art Room
$87 NZD per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Urban Comfort in the Heart of Chicago
$85 NZD per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$135 NZD per night
PLUS
  1. Entire rental unit
  2. Chicago
Eclectic Artist Designed Sanctuary Heart of Pilsen
$165 NZD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Beautiful and spacious West Loop apartment.
$251 NZD per night