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Vacation rentals in Downtown Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Downtown Chicago

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

Superhost
Apartment in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.
ﺩ.ﺇ406 per night
Superhost
Home in Wicker Park
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
ﺩ.ﺇ364 per night
Superhost
Apartment in Magnificent Mile
☀️Amazing Gold Coast Apt w/ Rooftop Pool & Gym☀️
Located in the heart of Gold Coast, Chicago's most sought after neighborhood. Please enjoy our large, brand new rehabbed apartment unit with an amazing open floor plan. The unit offers a brand new updated kitchen, living room, bedroom, bathroom and a beautiful lobby and hallways. The building offers amazing amenities including a pool on the 24th floor rooftop, patio furniture with grills on the rooftop, a brand new rehabbed gym and study space.
ﺩ.ﺇ421 per night

Other great vacation rentals in Downtown Chicago

Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
ﺩ.ﺇ485 per night
Superhost
Apartment in Gold Coast
Spectacular Penthouse Corner 2BR in Streeterville
ﺩ.ﺇ557 per night
Superhost
Apartment in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
ﺩ.ﺇ215 per night
Superhost
Apartment in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
ﺩ.ﺇ621 per night
Superhost
Apartment in Lincoln Park
Sophisticated Flat in Historic Building
ﺩ.ﺇ588 per night
Superhost
Apartment in West Town
Explore the City from an Elegant, Urban Retreat
ﺩ.ﺇ451 per night
Superhost
Apartment in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
ﺩ.ﺇ320 per night
Superhost
Apartment in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
ﺩ.ﺇ472 per night
Superhost
Apartment in Near North Side
50th Floor Mag Mile Studio
ﺩ.ﺇ435 per night
Superhost
Condo in The Loop
1BA Premium Downtown Location!Riverwalk & Mag Mile
ﺩ.ﺇ485 per night
Superhost
Apartment in Magnificent Mile
Simple and Cozy Studio Apartment
ﺩ.ﺇ209 per night
Superhost
Condo in The Loop
Luxe Condo In DT Chicago w/ Fast Wi-fi, Pool, Gym
ﺩ.ﺇ283 per night

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