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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.

Superhost
Flat 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.
Individual Host
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).
Professional Host
Superhost
Flat 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.
Professional Host

Other great holiday rentals in Downtown Chicago

Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
Individual Host
Superhost
Flat in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
Individual Host
Superhost
Flat in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
Individual Host
Superhost
Flat in Gold Coast
Stunning Corner 2BR in Streeterville | Roof Deck |
Professional Host
Superhost
Flat in West Town
Explore the City from an Elegant, Urban Retreat
Professional Host
Superhost
Flat in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
Individual Host
Superhost
Flat in Lincoln Park
Sophisticated Flat in Historic Building
Individual Host
Superhost
Flat in Near North Side
50th Floor Mag Mile Studio
Individual Host
Superhost
Apartment in The Loop
1BA Premium Downtown Location!Riverwalk & Mag Mile
Professional Host
Superhost
Flat in Magnificent Mile
Simple and Cozy Studio Apartment
Individual Host
Superhost
Flat in Old Town
Breathtaking & Chic Oasis Loc in Desirable Old Twn
Individual Host
Superhost
Apartment in The Loop
Luxe Condo In DT Chicago w/ Fast Wi-fi, Pool, Gym
Individual Host

Destinations to explore

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