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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.

₹9,946 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

₹10,673 per night
  1. Private room
  2. Chicago
Downtown/Lake/Soldier Field Paradise Haven

Enjoy a beautiful and very neat condo with 2 private bedrooms, 2 private bathrooms, a large living room, and a patio that sees directly Soldier Field Stadium, a glimpse of Lake Michigan, and Downtown view

₹11,537 per night

Holiday rentals for every style

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Stay near Downtown Chicago's top sights

Photo of Millennium Park
Millennium Park473 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. Private room
  2. Chicago
Gold Coast (Downtown) Cozy private room.
₹4,149 per night
  1. Entire apartment
  2. Chicago
NEW LISTING - King bed suite with hot tub
₹9,400 per night
  1. Hotel room
  2. Chicago
Hotel Perks - Private Bedroom | Private Bathroom
₹13,481 per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Bridgeport LR Renovated Loft Studio MONTHLY
₹3,183 per night
  1. Entire rental unit
  2. Chicago
New Spot in West Town
₹8,093 per night
  1. Entire guest suite
  2. Chicago
Cozy one-bedroom suite in the heart of West Loop
₹8,684 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
₹10,173 per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
₹6,524 per night
SUPERHOST
  1. Entire guest house
  2. Chicago
Private Studio in Bridgeport, Chicago
₹6,104 per night
  1. Private room
  2. Chicago
Stunning downtown High Rise apartment amazing view
₹9,094 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
₹7,957 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Millennium Park Paradise (2BD/2BA)
₹11,776 per night
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago