Chicago skyline guide

Chicago's skyline is one of the world's tallest and easily ranks among its most magnificent. It boasts several of the tallest buildings in the Western Hemisphere, including the massive Sears Tower, which was for much of the 20th century the tallest building in the world, and remains right near the top of such lists.


X-bracing on the John Hancock Center

See Architecture for more on Chicago's skyscrapers and some of their shorter, notable counterparts.

In the late 19th century, Chicago's downtown was an ideal location for architects of ambition; the Great Chicago Fire of 1871 had literally gutted the downtown area, creating a relentless drive to re-build and ample space in which to do it. Chicago's engineers solved the problem of the load-bearing wall, liberating structures from the limits of what a masonry foundation could support. Built in 1885, William LeBaron Janney's 10-story Home Insurance Building was the first to use a steel-frame skeleton to support its walls — at one-third of the weight of a structure using conventional means. Real estate prices and building heights soared in the years that followed, but the boom years of the 1920s financial bubble saw an unprecedented wave of skyscrapers that shattered previous records for size, including the still-extant Mather Tower, Tribune Tower, and later the Chicago Board of Trade.

The second wave, oddly enough, occurred during the 1960s and 70s, when urban centers across America were experiencing white flight and severe population decline. The answer of Chicago's first Mayor Daley was simple: build, and then build some more. As a result, while the residential population spread across a wide range of suburbs, commercial activity remained fixed at the center of the city. It was during this time when Chicago gained its most famous modern skyscrapers, including the three of the tallest: the Sears Tower, the Aon Center, and the John Hancock Center. (It was also during this time — as occurred during the first wave — when a giant swathe of early skyscrapers were recklessly demolished.)

The third wave of supertall construction hit in the beginning of the 21st century. Driven by downtown Chicago's residential real estate boom (the hottest in the country prior to the 2007–2008 financial crisis), existing buildings converted office space to condominiums and hotels, and builders raced to erect some of the world's tallest buildings, which have radically re-shaped the city's skyline. The most obvious result of the building spree is, of course, the Trump Tower, now the third tallest building in the U.S., and second in Chicago only to the Sears Tower. Following the financial crisis, though, construction on several very high profile buildings ground to an abrupt halt as virtually all sources of credit dried up, rendering some of the most intriguing projects mere flights of fancy, relegated to the dustbin of counterfactual history, including the once highly anticipated Chicago Spire.


Using this guide, you should be able to figure out what buildings you are looking at from any of Chicago's most popular skyline-gazing spots. The CTA Red Line is the best means for reaching most of the viewing points that follow; see individual district articles for more detailed directions.

The most popular views of Chicago's skyline are over Lake Michigan from the east. The two main locations for easterly views are:

The Loop view from Adler Planetarium:

and the Near North Side view from Navy Pier:

The clearest view from the North Side is at Uptown's Montrose Point:

The most popular view from the South Side is at US Cellular Field:

And a typical West Side view can be found at Ashland L Station on the CTA Green/Pink Line, near the United Center:

But perhaps even more remarkable are the views from the skyline itself, particularly the John Hancock Center Observatory:

and the Sears Tower Skydeck:


The following is a reference list of Chicago skyscrapers, in descending order by height, listed on the views maps. For directions, maps and information for buildings that are open to visitors, see individual district articles. All but one of these buildings can be found in the Loop and the Near North.

The top ten

Shorter, but proud

Even shorter, but still rising above the crowd

Last, but not least

Under construction

After the events of September 11, 2001, it was proposed that the era of the super-tall skyscraper was over; people did not want to live or work in what were, essentially, big attack targets. Funding dried up for a while, and modest designs were the word of the day.

That didn't last long. Chicago is too wrapped up in the idea of the skyscraper to stop building them, and in time, the economic backing returned: Chicago's downtown underwent an unprecedented residential real estate and construction boom over the next six years, leading Forbes Magazine to declare the 60602 zip code the hottest in the country. Things slowed down following the financial collapse, but the air is still filled with cranes and scaffolding and dreams—expect the construction to pick up faster than the economy.

Real estate recovery seems no longer a matter of speculation as of 2013, with a ream of new supertall constructions beginning. Perhaps the most anticipated project of late is the set of three skyscrapers slated to go up on Wolf Point at the western bend of the Chicago River downtown, with the tallest registering at 950 ft. That will make for a busy section of town, given the construction of 650 ft River Point just across the river!

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