The Bucket List: An Architecture Lover's Guide to Chicago

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When much of the city’s business district burned in 1871—in what became known as the Great Chicago Fire—Chicago was left in ruins. A horrific event, no doubt, but from the ashes rose some of the country’s most iconic and significant works of architecture, including the world’s first skyscraper.

Architects from around the world came to Chicago to leave their mark on the city’s blank canvas. Today, Chicago remains a living museum to relics of Daniel Burnham, John Root, Louis Sullivan, Charles B. Atwood and Ludwig Mies van der Rohe and it continues to serve as a canvas for modern architecture greats like Jeanne Gang, Frank Gehry and Helmut Jahn, among others.

October marked the start of the Chicago Architecture Biennial, which is the perfect excuse to not only witness, but appreciate the city’s legacy, starting with these nine buildings every architecture lover must see when visiting Chicago.

1. Thompson Center

100 W. Randolph Street

Photo by Mobilus In Mobili, CC BY 2.0

The James R. Thompson Center has been loved and hated equally by Chicagoans since it opened in 1985. The Helmut Jahn-designed facility occupies an entire city block in Chicago’s Loop and currently houses Illinois state government offices. The shape and glass facade of this 17-story building has been compared to a spaceship. The large open atrium inside is one of its most impressive features and is home to dozens of shops and restaurants. Recently, Illinois Governor Bruce Rauner made waves by proposing to sell the building potentially for demolition, which was greeted by cheers and jeers from those who hold the building in varying regards. Just in case, it’s better to see it in person sooner than later.

2. Sears Tower (Willis Tower)

233 S. Wacker Drive

Photo by Ashley Diener, CC BY-NC-ND 2.0

No building in Chicago is more famous than Willis Tower (formerly, and forever in the hearts of Chicago natives, known as the Sears Tower). Defining the Chicago skyline since 1973, this 108-story tower for a time held the record as the tallest building in the world. Today, it remains the second tallest in the country and its Skydeck on the 103rd floor provides incredible panoramic views of Chicago, as well as the surrounding area and Lake Michigan.

3. Marina City

300 N. State Street

Photo by clarkmaxwell, CC BY-NC-ND 2.0

Indie music fans outside of Chicago might recognize Marina City. It graced the 2002 cover of Wilco’s Yankee Hotel Foxtrot album. The 65-story twin towers were designed by architect Bertrand Goldberg and since 1964 have served as both apartments and an icon of Chicago. This year, Marina City received preliminary landmark status by the Commission on Chicago Landmarks, an important and exciting step toward preservation. Besides its residents, Marina City is also home to the House of Blues Chicago, a bowling alley, as well as several restaurants.

4. The Rookery Building

209 S. LaSalle Street

?Photo by Jamie McCaffrey, CC BY 2.0

Undoubtedly among Chicago’s most significant architectural masterpieces and one of its most historical buildings, The Rookery was built in 1886 and remains the oldest high-rise in the city. It was designed by John Root and Daniel Burnham, the latter of which served as Director of Works for the 1893 World’s Columbian Exposition. Burnham and Root housed the offices of their architecture firm in the building, and it was there that they reviewed drawings and plans for what would come to be known as the White City of the World’s Fair. As if that doesn’t bolster The Rookery’s importance enough, Frank Lloyd Wright redesigned the lobby in 1905 leaving his mark on downtown Chicago.

5. Tribune Tower

435 N. Michigan Avenue

Photo by Zen Skillicorn, CC BY-ND 2.0

This neo-Gothic beauty was the result of a design competition won by New York-based architects John Mead Howells and Raymond Hood. Howells and Hood, a restaurant at the building’s base, is named in their honor. The building is also home to the Chicago Tribune, WGN radio, and CNN’s Chicago bureau, among other important media outlets. This landmark tower’s beauty is very much in the details. If you visit, be sure to circle the exterior of Tribune Tower to see fragments of famous structures collected from around the world and incorporated as reliefs in the building’s facade. There are 149 fragments in all, including pieces of the Taj Mahal, Colosseum, World Trade Center, Great Pyramid at Giza, Berlin Wall, Great Wall of China, Angkor Wat, as well as the Notre Dame Cathedral.

6. Jay Pritzker Pavilion

201 E. Randolph Street

Photo by Jackman Chiu, CC BY-NC-ND 2.0

In the heart of Millennium Park you’ll find the 11,000-capacity Jay Pritzker Pavilion. The outdoor amphitheater was designed by renowned architect Frank Gehry and serves as home to the Grant Park Symphony Orchestra, as well as host to major national and international touring acts. During summer, Pritzker Pavilion is also the site of the Grant Park Music Festival, the only free outdoor classical music festival in the country.

7. Wrigley Building

400 N. Michigan Avenue

Photo by Tom Gill, CC BY-NC-ND 2.0

The Wrigley Building, which sits prominently on Michigan Avenue in the company of the Trump International Hotel and Tower and Tribune Building, broke ground in 1920 to serve as the headquarters of its namesake company. Since then, the building’s dual towers have served as home to countless major corporate offices and even a few consulates. The combined above ground footprint equals an impressive 453,433 square feet, which can’t be missed. At night, this stately beauty is bathed in bright flood lights so those passing by can marvel at it.

8. Aqua

225 N. Columbus Drive

Photo by clarkmaxwell, CC BY-NC-ND 2.0

Among Chicago’s modern architectural marvels is the Jeanne Gang-designed Aqua. This 80-story mixed-use skyscraper includes condos, apartments, as well as a hotel. The facade of the tower features irregularly shaped balconies that give the building a wave-like appearance—hence the name.

9. Museum of Science and Industry

5700 S. Lake Shore Drive

Photo by Brandon O’Connor, CC BY-SA 2.0

The Museum of Science and Industry is the only remaining building in the city from the 1893 World’s Columbian Exposition. It was designed by Charles B. Atwood and during the fair served as the Palace of Fine Arts. Fans of Erik Larson’s New York Times bestselling nonfiction novel Devil in the White City will appreciate seeing it in person, and the museum it houses is one of Chicago’s best.

Tip : If you’re not looking to tackle Chicago’s architecture in self-guided exploration, the Chicago Architecture Foundation has an assortment of tours and programs, including their wildly popular boat tours, that serve as a great education on the city’s most significant structures.

Top photo: Jonathan, CC BY-NC-ND 2.0

Paste Travel’s Bucket List columnist Lauren Kilberg is a Chicago-based freelance writer. Her travels have found her camping near the Pakistani border of India and conquering volcanoes in the Philippines.