Vacation 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

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.

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).

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.