Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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

SUPERHOST
  1. Entire rental unit
  2. Chicago
Millennium Park Paradise

Located in Chicago's Loop, this large 2 bedroom, 2 bathroom is in the heart of all things Chicago. Theatres, shopping, great restaurants, nightlife, parks and Lake Michigan are all nearby!

  1. Private room
  2. Chicago
Private Room in Great Location to City

Private, VERY CLEAN room 5 minutes to downtown with FREE PARKING, GREEN TEA & ALOE memory foam mattress, and an EARLY check-in (11 a.m.). You will have your own door code and may arrive at ANY time and as late as you wish, EASY self check-in guaranteed. I allow LUGGAGE DROP OFF! You can store your luggage in the closet before check-in and after check-out times, you can drop it off and pick it up as early and as late as you would like. The neighborhood is extremely safe even at night :) 


SUPERHOST
  1. Entire rental unit
  2. Chicago
Theater District Hideaway

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 1 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, the Bean, Navy Pier, Riverwalk, and museum campus. Additionally, guests are merely a block from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Vacation rentals for every style

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Stay near Downtown Chicago's top sights

Photo of Millennium Park
Millennium Park474 locals recommend
Photo of Navy Pier
Navy Pier306 locals recommend
Photo of Willis Tower
Willis Tower151 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago436 locals recommend
Photo of Skydeck Chicago
Skydeck Chicago51 locals recommend

Other great vacation rentals in Downtown Chicago

SUPERHOST
  1. Private room
  2. Chicago
Gold Coast (Downtown) Cozy private room.
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Private Studio in Bridgeport, Chicago
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
  1. Entire guest suite
  2. Chicago
Cozy one-bedroom suite in the heart of West Loop
  1. Private room
  2. Chicago
Single Bedroom w/ Twin Bed & 5min to Metro
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
  1. Private room
  2. Chicago
Stunning downtown High Rise apartment amazing view
SUPERHOST
  1. Private room
  2. Chicago
Chicago Speakeasy-Style Loft Space (Room 3A)
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport LR Renovated Loft Studio MONTHLY
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft, Private Room
  1. Private room
  2. Chicago
Lovely private bedroom in Fantastic location
SUPERHOST
  1. Private room
  2. Chicago
Chicago Speakeasy-Style Loft Space (Room 1A)
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago