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Holiday 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.

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.

$171 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy Studio With Beautiful Lake View with Parking

Enjoy a stylish experience at this centrally-located place. Studio close to Adler Planetarium, Field Museum, Shedd Aquarium, and Soldier Field. Navy Pier just minutes away. Enjoy a nice walk down Michigan Ave to Grant State Park. Studio fully equipped with: WiFi Tv Netflix, Hulu Travel size shower amenities Toothbrush Feminine hygiene products Hair Dryer Hair Straightener Clothes steamer Keurig Sofa bed Parking available in public paid parking garage across the street

$180 SGD per night
SUPERHOST
  1. Entire loft
  2. Chicago
Grand Studio in the Heart of Lakeview!

NEW Listing: Artsy loft style studio in Lakeview; steps from the Belmont Red/Brown/Purple Lines. Quiet interior unit, high 15ft concrete ceilings, dishwasher, multi-view wall mounted TV, full size murphy bed, and walk in closet. Gorgeous Rooftop views. Close to Wrigley Field, Lakeshore Drive, Target, and Whole Foods. Twenty minute train ride to the loop.

$86 SGD per night

Holiday 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 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 Chicago437 locals recommend
Photo of Skydeck Chicago
Skydeck Chicago52 locals recommend

Other great holiday rentals in Downtown Chicago

SUPERHOST
  1. Entire rental unit
  2. Chicago
1bed/1bath !Location! Steps to South Loop Apt
$34 SGD per night
  1. Entire apartment
  2. Chicago
NEW LISTING - King bed suite with hot tub
$164 SGD per night
  1. Private room
  2. Chicago
Private Room in Great Location to City
$93 SGD per night
  1. Hotel room
  2. Chicago
Hotel Perks - Private Bedroom | Private Bathroom
$250 SGD per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Bridgeport LR Renovated Loft Studio MONTHLY
$55 SGD per night
  1. Entire guest suite
  2. Chicago
Cozy one-bedroom suite in the heart of West Loop
$132 SGD per night
  1. Entire rental unit
  2. Chicago
New Spot in West Town
$132 SGD per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$172 SGD per night
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
$104 SGD per night
  1. Private room
  2. Chicago
Stunning downtown High Rise apartment amazing view
$157 SGD per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
$112 SGD per night
  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
$115 SGD per night
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  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago