Downtown Chicago vacation rentals

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Top-rated vacation rentals in Downtown Chicago

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

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Private room in Chicago

Chicago Speakeasy-Style Loft Space (Room 3A)

Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!

$116 per night

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Rental unit in Chicago

50th Floor Mag Mile Studio

This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.

$137 per night

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Private room in Chicago

Chicago Speakeasy-Style Loft Space (Room 2A)

Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with a lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings!

$120 per night