Here are 10 historymaking examples of Chicago architecture, and the many reasons why you should pay them a visit. Chicago is a key part of skyscraper history.Willis Tower has been an iconic part of the Chicago skyline since 1973. At 110 stories high, Willis Tower is also one of the largest skyscrapers in the world. Comments23 ; Top 10 Failed Skyscrapers. Orbitz has illustrated 20 of Chicago's most prominent skyscrapers to celebrate the city's love for skyhigh architecture.