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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.

Flat in Chicago
The Executive's Escape (2BD/2BA)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 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, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.
₹19,785 per night
Private room in Chicago
Chicago Speakeasy-Style Loft Space (Room 3A)
Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!
₹9,269 per night
Flat in Chicago
50th Floor Mag Mile Studio
This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.
₹13,879 per night

Other great holiday rentals in Downtown Chicago

Flat in Chicago
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
₹14,901 per night
Private room in Chicago
MAG MILE Private Bed/Bath in a LUX 2BR/2BA Apt
₹13,701 per night
Flat in Chicago
☀️❤️‍🔥Gold Coast Lavish Home w/ Roof Pool & Gym❤️‍🔥☀️
₹15,103 per night
Flat in Chicago
Kasa | Explore the Neighborhood-Mag Mile | Chicago
₹35,471 per night
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago