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
Sonder South Wabash | Superior One-Bedroom Apartment w/ Balcony
Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kitchen, in-suite laundry, and stunning Chicago views. Colorful art pieces complement the industrial exposed concrete ceilings. And floor-to-ceiling windows burst with natural night. There’s always something to do in the Windy City. Field Museum hosts fascinating exhibitions, Grant Park is perfect for a stroll, and South Michigan Avenue has the best restaurants. Victory Tap is around the corner and “Mama’s Meatballs” will leave your tasetbuds watering. Whether you like jazz, opera, or dive bar karaoke, the South Loop has entertainment for everyone. At South Wabash, the best of the city is on your doorstep.
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
Condo 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

Vacation rentals for every style

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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 vacation rentals in Downtown Chicago

Private room in Chicago
Chicago Speakeasy-Style Loft Suite (Room 2B)
Professional Host
SUPERHOST
Serviced apartment in Chicago
Modern Studio with Floor-to-Ceiling Windows
Rental unit in Chicago
Pilsen 2F *In-Unit Laundry* 2bed/1bath !Location!
Individual Host
SUPERHOST
Condo in Chicago
Charming Lincoln Park Duplex Apartment
Individual Host
SUPERHOST
Rental unit in Chicago
1BR West Loop Apt, In-Unit Laundry, Public Parking
Professional Host
Rental unit in Chicago
1BR Perfect Home in the City, Close to Everything
Professional Host
Rental unit in Chicago
!3R Location! 2bed/2bath StepstoSouthLoop +Laundry
Individual Host
SUPERHOST
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
SUPERHOST
Rental unit in Chicago
Pilsen 3R 1bed/1bath + Free Laundry +GreatLocation
Individual Host
SUPERHOST
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
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Nearby destinations

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago