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Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

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

Other great vacation rentals in Downtown Chicago

Rental unit in Chicago
*Luxury High Rise, Clean Design/Balcony/Amenities!
$150 per night
Rental unit in Chicago
Steps to MI Ave Shops | View, Beach, Gym | Zencity
$98 per night
Condo in Chicago
McCormick Place Studio/parking/sleeps up to 4
$91 per night
SUPERHOST
Rental unit in Chicago
McCormick Place Studio/parking/sleeps up to 4
$88 per night
SUPERHOST
Rental unit in Chicago
McCormick 420 friendly 2br/2ba
$108 per night
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Rental unit in Chicago
McCormick Pl 420 friendly 1br/1ba parking/sleeps 4
$100 per night
Rental unit in Chicago
Peaceful & Complete 1BR Apt in West Loop
$67 per night
Private room in Chicago
Beautiful Private Room 5 min to downtown Chicago
$65 per night
Rental unit in Chicago
5-min to Downtown Chicago, near Pay Parking | 1BR
$67 per night
Rental unit in Chicago
Gorgeous & Centrally-Located 1BR Apt in West Loop
$67 per night
Rental unit in Chicago
1BR Luxury Apartment With Private Office, Terrace,
$140 per night
Private room in Chicago
Downtown/Lake/Soldier Field Paradise Haven
$109 per night
SUPERHOST
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