Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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Rental unit in Chicago

52nd Floor MagMile Penthouse Views Fireplace Pool

ThiThis Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with floor to ceiling window in with a the spacious open floor plan living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. The city unfolds before 52 floors above a Lake Michigan backdrop; nowhere in Chicago can you stay with views like theses special place is close to everything, making it easy to plan your visit.

$176 per night

SUPERHOST

Condo in Chicago

Private hot tub and king bed suite

Welcome to this historic yet chic retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best entertainment, museums, shopping, food and nightlife the city has to offer. At the end of your day, enjoy a relaxing soak in your private outdoor patio hot tub before sinking in to your Tempur-Pedic king bed for a restful night's sleep.

$113 per night

SUPERHOST

Rental unit in 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.

$130 per night