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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.
$109 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).
$99 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.
$139 per night

Other great vacation rentals in Downtown Chicago

Superhost
Apartment in Gold Coast
Spectacular Penthouse Corner 2BR in Streeterville
$150 per night
Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
$132 per night
Superhost
Apartment in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
$169 per night
Superhost
Apartment in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$59 per night
Superhost
Apartment in Lincoln Park
Sophisticated Flat in Historic Building
$160 per night
Superhost
Apartment in West Town
Explore the City from an Elegant, Urban Retreat
$128 per night
Superhost
Apartment in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
$87 per night
Superhost
Apartment in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
$128 per night
Superhost
Apartment in Near North Side
Great Location Studio III
$64 per night
Superhost
Apartment in Near North Side
50th Floor Mag Mile Studio
$127 per night
Superhost
Condo in The Loop
1BA Premium Downtown Location!Riverwalk & Mag Mile
$134 per night
Superhost
Apartment in Magnificent Mile
Simple and Cozy Studio Apartment
$57 per night

Destinations to explore

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