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Downtown Downtown Chicago vacation rentals

Book unique condos, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Downtown Chicago

Guests agree: these vacation rentals 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!

G$31,407 per night
  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 :) 


G$13,042 per 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.

G$26,173 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Downtown Chicago's top sights

Photo of Millennium Park
Millennium Park475 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

Downtown Chicago vacation rentals

  1. Hotel room
  2. Chicago
Hotel Perks - Private Bedroom | Private Bathroom
G$37,180 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft, Private Room
G$23,212 per night
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Private Studio in Bridgeport, Chicago
G$15,136 per night
  1. Entire guest suite
  2. Chicago
Cozy one-bedroom suite in the heart of West Loop
G$22,883 per night
  1. Private room
  2. Chicago
Single Bedroom w/ Twin Bed & 5min to Metro
G$6,910 per night
  1. Private room
  2. Chicago
Stunning downtown High Rise apartment amazing view
G$23,930 per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
G$17,169 per night
SUPERHOST
  1. Private room
  2. Chicago
Chicago Speakeasy-Style Loft Space (Room 3A)
G$20,729 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
G$20,938 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport LR Renovated Loft Studio MONTHLY
G$8,375 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
G$24,018 per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★ ..
G$17,797 per night

Downtown Chicago summer vacation rentals

SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #207 at 747 Lofts
G$14,238 per night
  1. Entire rental unit
  2. Chicago
DOWNTOWN STUDIO BY RUSH STREET -GOLD COAST CENTER
G$25,934 per night
SUPERHOST
  1. Private room
  2. Chicago
Hotel quality room near Downtown,CTA, McCormick
G$10,469 per night
  1. Private room
  2. Chicago
Contemporary, private suite w fireplace
G$13,461 per night
  1. Private room
  2. Chicago
Private Bedroom near Downtown Chicago Chinatown
G$9,361 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport 2R Renovated 2bed/1bath Apt. MONTHLY
G$8,375 per night
  1. Private room
  2. Chicago
Private Room A5 by Chinatown
G$6,910 per night
SUPERHOST
  1. Private room
  2. Chicago
Downtown Chicago 8 minutes away SELF CHECK IN
G$8,436 per night
  1. Private room
  2. Chicago
Goose & Fox Hostel Lincoln Park
G$10,708 per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Bridgeport LF Renovated Loft Studio MONTHLY
G$8,375 per night
  1. Private room
  2. Chicago
Rustic Private BR - 5 min to Chinatown & Downtown
G$10,140 per night
  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
G$19,292 per night

Downtown Chicago holiday vacation rentals

  1. Private room
  2. Chicago
Private Room in GREAT LOCATION to CITY
G$17,079 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #103 at 747 Lofts
G$10,260 per night
SUPERHOST
  1. Private room
  2. Chicago
B5Hotel quality room near Downtown, CTA,McCormick
G$9,422 per night
  1. Private room
  2. Chicago
City View near Downtown Chicago Sox Chinatown
G$11,068 per night
  1. Private room
  2. Chicago
Cleanest & Newest place near Downtown Chicago
G$7,358 per night
  1. Private room
  2. Chicago
Rustic Private BR - 5 min to Chinatown & Downtown
G$9,422 per night
  1. Entire rental unit
  2. Chicago
1 Bedroom Apartment by McCormick Place & Chinatown
G$13,490 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport 2F Renovated 2bed/1bath Apt. MONTHLY
G$11,665 per night
  1. Private room
  2. Chicago
Rustic BR w/ full size bed - 2 min Walk to CTA
G$10,320 per night
SUPERHOST
  1. Private room
  2. Chicago
🌟 Cozy Bedroom by Downtown & Train; Rooftop Deck!🌟
G$12,111 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Fully Furnished Apartment Wicker Park Free Parking
G$25,126 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Millennium Park Paradise (2BD/2BA)
G$34,129 per night
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago