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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.

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.
ﺩ.ﺇ100 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.
ﺩ.ﺇ392 per night
SUPERHOST
Private room in Chicago
Chicago Speakeasy-Style Loft Suite (Room 2B)
Welcome to our Chicago Speakeasy-style loft space. Built in the 1890’s our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with a lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings!
ﺩ.ﺇ315 per night
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 Pier63 locals recommend
Photo of Buckingham Fountain
Buckingham Fountain86 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

Rental unit in Chicago
Explore Chicago from an Urban Sanctuary with Free Parking
ﺩ.ﺇ165 per night
PLUS
Rental unit in Chicago
3R Location! 2bed/2bath Apt Steps from South Loop
ﺩ.ﺇ164 per night
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Hotel room in Chicago
Staypineapple Chicago, Deluxe King
ﺩ.ﺇ364 per night
Rental unit in Chicago
Hip Chicago Apartment - FREE Parking Spot Included
ﺩ.ﺇ88 per night
Rental unit in Chicago
Short-Term Sublet Near Lake Michigan
ﺩ.ﺇ154 per night
SUPERHOST
Condo in Chicago
Charming Lincoln Park Duplex Apartment
ﺩ.ﺇ335 per night
SUPERHOST
Rental unit in Chicago
1R Location! 1bed/1bath Steps to South Loop Apt
ﺩ.ﺇ132 per night
SUPERHOST
Rental unit in Chicago
2F Location! Steps from South Loop 1bed/1bath Apt.
ﺩ.ﺇ246 per night
SUPERHOST
Rental unit in Chicago
10% Winter Promo! Goose Island Well-Decorated 1BR
ﺩ.ﺇ225 per night
Rental unit in Chicago
Bridgeport_cp 3R Renovated 2bed/1bath Apt 32+nite
ﺩ.ﺇ262 per night
SUPERHOST
Rental unit in Chicago
1F Location! 2bed/1bath Steps to South Loop Apt
ﺩ.ﺇ250 per night
SUPERHOST
Condo in Chicago
Vintage Gem in West Town
ﺩ.ﺇ196 per night
SUPERHOST
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