Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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

Private room in Chicago

Remote Workers Dream - Private Bath and Workspace

Are you a professional remote worker or a digital nomad looking to explore Chicago? If so I made this listing for you! Welcome to my home one block from the Blue Line which runs 24/7 downtown and to O'Hare and a straight shot to Wrigley Field. You will have a clean cozy room, a private renovated bathroom, and a SECOND light-filled room to work or relax with a desk, chair, and TV. I live across from a beautiful park and have a backyard for BBQs and chilling. High-speed WIFI for your work!

$61 per night

SUPERHOST

Private room in Chicago

Logan Square Vintage Deluxe Private Suite & Bath

A private vintage haven - bedroom, bath and living space - in the heart of Logan Square. Surrounded by great shopping, food, cafes and bars, with easy travel to downtown. We follow the Airbnb guidelines for enhanced cleaning, and expect you are vaccinated, to ensure a safe visit for all. Kitschy and cool, cozy and comfortable - a walk up, second floor, private suite in a classic Chicago Victorian frame house on a quiet neighborhood street. A small, separate entry space that's all yours.

$91 per night

SUPERHOST

Private room in Chicago

A+ location by Mag Mile, views, large sunny room

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. Apartment is shared with single host (covid-vaccinated), happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/respectful host, Flexible luggage policy, fast wifi)

$89 per night

SUPERHOST