Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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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