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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
McCormick Place Studio/parking/sleeps up to 4
• Please MESSAGE US for SPECIAL WINTER RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • Minutes to all touristic destinations • Optional Parking space for only $25/day
$92 per night
SUPERHOST
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.
$164 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.
$127 per night

Other great vacation rentals in Downtown Chicago

Rental unit in Chicago
Steps to MI Ave Shops | View, Beach, Gym | Zencity
$89 per night
Condo in Chicago
Amenities No Hotel Room Can Match! Full Kitchen and In-Unit Laundry! - 747 Lofts Cabin 306
$65 per night
SUPERHOST
Condo in Chicago
McCormick Place Studio/parking/sleeps up to 4
$99 per night
SUPERHOST
Rental unit in Chicago
1-bedroom rental with a great view!
$97 per night
Rental unit in Chicago
1BR Luxury Apartment With Private Office, Terrace,
$119 per night
Rental unit in Chicago
*Luxury High Rise, Clean Design/Balcony/Amenities!
$150 per night
Private room in Chicago
Private room in apartment in Fantastic location
$60 per night
Rental unit in Chicago
McCormick 420 friendly 2br/2ba
$151 per night
SUPERHOST
Rental unit in Chicago
McCormick Pl 420 friendly 1br/1ba parking/sleeps 4
$92 per night
Rental unit in Chicago
Peaceful & Complete 1BR Apt in West Loop
$74 per night
Rental unit in Chicago
Gorgeous & Centrally-Located 1BR Apt in West Loop
$74 per night
Rental unit in Chicago
Uplifting Studio Apartment in Belmont
$41 per night
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  5. Downtown Chicago