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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.

Home in Chicago
Exclusive and Spacious Pilsen Guest House
Trendy and spacious private home with two bedrooms each with a queen-sized bed. located in the Center of Pilsen neighborhood named "the most vibrant neighborhood in Chicago". Walking distance to 18th street where all bars and restaurant . This elegant and meticulously maintained interior is complemented by stylish furniture and art all for your pleasure. Enjoy your own workspace to catch up on e-mails or relax while watching all your favorite shows on the SmartTV with complimentary Netflix.
Professional Host
SUPERHOST
Apartment in Chicago
GLORIOUS GOLD COAST GETAWAY
Welcome! Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!
Individual Host
SUPERHOST
Apartment 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.
SUPERHOST

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Stay near Downtown Chicago's top sights

Photo of Cloud Gate
Cloud Gate473 locals recommend
Photo of Millennium Park
Millennium Park1,244 locals recommend
Photo of Navy Pier
Navy Pier927 locals recommend
Photo of Buckingham Fountain
Buckingham Fountain219 locals recommend
Photo of Museum Campus
Museum Campus13 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago1,159 locals recommend

Other great holiday rentals in Downtown Chicago

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Sonder South Wabash | Superior One-Bedroom Apartment w/ Balcony
Private room in Chicago
Chicago Speakeasy-Style Loft Suite (Room 2B)
Professional Host
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Rental unit in Chicago
Explore Chicago from an Urban Sanctuary with Free Parking
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PLUS
Apartment in Chicago
Charming Lincoln Park Duplex Apartment
Individual Host
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Rental unit in Chicago
!3R Location! 2bed/2bath StepstoSouthLoop +Laundry
Individual Host
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Rental unit in Chicago
Sentral Studio Apt in South Loop Chicago
Professional Host
Rental unit in Chicago
!2F Location! 1bed/1bath StepstoSouthLoop +Laundry
Individual Host
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Rental unit in Chicago
!1F Location! 2bed/1bath StepstoSouthLoop +Laundry
Individual Host
SUPERHOST
Rental unit in Chicago
Bridgeport_cp 3R 2bed/1bath + Free Laundry
Individual Host
SUPERHOST
Private room in Chicago
Room T5
Individual Host
Private room in Chicago
Room T6
Individual Host
Rental unit in Chicago
!2R Location! 2bed/2bath StepstoSouthLoop +Laundry
Individual Host
SUPERHOST
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago