The 50 most beautiful buildings in Chicago

We searched Chicago's skyline from the skyscrapers to the side streets (and beyond) to find our favorite examples of the city's architectural excellence

By Time Out Chicago editors

Posted: Friday October 13 2017

Photograph: Courtesy of the Chicago Architecture Foundation
Wrigley Building

It’s easy to find exemplary architecture in Chicago, whether you’re admiring the skyline from Lake Michigan or taking a stroll through the streets of a neighborhood. After a large section of the city burnt to the ground in 1871, architects went to work rebuilding Chicago on a grand scale, erecting classic buildings like the Tribune Tower and the Chicago Cultural Center.

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The architectural innovation hasn’t slowed down since, with recent projects like Aqua Tower and the Joe and Rika Mansueto Library cementing Chicago’s status as a hotbed of innovative structures. Even the city’s historical buildings are being put to new uses, housing stores, bars and restaurants that allow visitors to experience a part of the area’s architectural history. We went on a few boat tours, consulted some experts and explored the city to assemble our list of 50 of Chicago’s most beautiful buildings.

The 50 most beautiful buildings in Chicago, ranked

The definitive (not really) ranking

The experts’ picks

We asked professors, architects and traffic reporters to name their top Chicago buildings

Readers’ poll

We’ve told you which buildings are the most beautiful. But do you agree? Have your say

Beautiful buildings by the numbers

We break down our favorite architecture by height, age and style

Chicago’s 15 ugliest buildings

We’re ready to erase these architectural misfires from our city’s skyline

Chicago’s best boat tours

Tired of walking around town? Get your float on with these nautical excursions