A paper tour of the Chicago skyline


Chicago became the birthplace of the skyscraper when the whopping 10-story tall Home Insurance Company building was built in 1884. Prior to that year, all buildings were only five stories, so the building at the corner of LaSalle and Adams revolutionized architecture. Chicago has continued to create visually interesting and architecturally astonishing buildings and is home to four of America’s 10 tallest buildings. As a historically imperative city in the creation of the modern day city skyline, here is your guide to the 26 buildings of Chicago’s skyline.

311 S. Wacker

311 S. Wacker is the first building in the skyline on the South Side of the city. At 961 feet to the tip of the building, 311 is the seventh tallest building in Chicago and the 22nd tallest in United States. The 67-story building was completed in 1990 and has 34 elevators.

Willis Tower

The second building in the skyline is also the tallest building in Chicago and the 14th tallest building the world; the Willis Tower is a Chicago staple. At its completion in 1974, the Willis Tower was the tallest building in the world, holding that record for 25 years before One World Trade Center in New York City beat it out. The tower is a popular tourist attraction because of Sky Deck and its appearance in “Ferris Bueller’s Day Off”. The first 50 floors of the tower take up a full city block, before it narrows at floor 51. The building has 104 elevators and reaches a total height of 1,729 feet.

Chicago Board of Trade

Built in the 1920’s, the Chicago Board of Trade is one of Chicago’s oldest skyline buildings, as well as a classic example of Art Deco. Just like the Willis Tower, the building was the tallest building in Chicago at its completion.

CNA Plaza

Recognized as the giant red building in the Chicago Skyline, the building is home to CNA Insurance and is right next to DePaul’s Loop Campus. The building is only 601 feet tall, with 44 floors, but stands out with its red facade.

Chase Tower

Chase Tower is the ninth tallest building in Chicago, located on Madison Street. The building, which consists of 61 floors, is known for the curve in the building and the public space outside of the building, which features a plaza and a ceramic wall mural.

Crain Communications Building

Built in 1983, the building is an iconic skyscraper across the street from Maggie-Daley Park. The building is known for its rhombus shape, declining roof and how it looks split down the middle. The building sometimes features slogans across the building supporting sports teams, elections and parades or marches.

Two Prudential Plaza

Two Prudential Plaza, located near the end of the skyline on the north side, is the sixth tallest building in Chicago and the 18th tallest in the United States. The building barely misses the 1,000 feet mark by five feet. Standing at 995 feet, the building was featured in the 1994 film “Richie Rich.”

Aon Center

Situated right next to Two Prudential Plaza, the Aon Center is the tall, all white building nearing the north part of the skyline. The building overlooks Millennium Park. The building is the third tallest in Chicago and seventh tallest in North America. With simplicity in structure and color, the Aon Center reaches about 1,200 feet, and has earned a quiet spot in the skyline.

875 N. Michigan

875 N. Michigan, otherwise known as the John Hancock Center, recognizable for the all black exterior, subtle slope and two antennas at the top, is an iconic building in the skyline. At the opposite end of the Willis Tower, the building is a product of its time. Built in the 1960’s, it’s a classic example of Chicago architecture. The building is the fourth tallest in Chicago and the eighth tallest in North America.