If you want to be factually correct, call it the Willis Tower. But many longtime residents who mourn the name change still say Sears Tower. Completed in 1973, the 1,450-foot tower is the undisputed king of the Windy City skyline. It held the title of the world’s tallest building for decades and maintained its claim to the highest roof in the Western Hemisphere up until last summer. Willis Tower is wrapping up a $500 million makeover which includes a new food hall, glass skylight, and revamped retail complex.

It is difficult to visualize the Chicago skyline without the famous supertall, formerly named John Hancock Center, now known by its address. Sharing many similarities with the Willis Tower, the SOM-designed skyscraper is perhaps the best example of structural expressionism. Rising 1,128 feet to the roof and nearly 1,500 feet to the tip of its twin antennas, the building was one of the tallest buildings in the world when it was completed in 1969. 

Originally known as the Standard Oil Building or “Big Stan,” Chicago’s third tallest skyscraper was later renamed the Amoco Building and, ultimately, the Aon Center. Completed in 1973, the monolithic office tower’s white facade was initially wrapped in 43,000 thin slabs of Italian Carrara marble. It was later re-clad in white granite after the marble started falling off the building and was deemed structurally unsafe. There’s also plans for a third observatory with a “thrill ride” and a glass elevator at 1,185 feet.

The design of this famous skyscraper was the winning submission from John Mead Howells and Raymond Hood in a 1922 competition held by the Chicago Tribune newspaper. In addition to its notable neo-Gothic design, the structure features fragments from some the world's most famous structures—the Taj Mahal, Great Wall of China, Angkor Wat, and the Great Pyramids—embedded in its exterior. Big changes are coming to the landmark building as workers convert it into 162 luxury condos and a nearby supertall skyscraper.

Just across from the Tribune Tower is another one of Chicago’s most famous early skyscrapers—the Wrigley Building. Built by the Wrigley Company in the early ’20s, the terra cotta complex actually consists of two buildings: a 30-story south tower connected to a 21-story north tower via a 14th-floor elevated walkway. The riverfront structure was also Chicago’s first air-conditioned office building.

Designed by visionary architect Bertrand Goldberg and completed in 1968, Marina City was the original city-within-a-city development. Perched on the edge of the Chicago River, the Brutalist complex suddenly made it cool to live downtown and included innovative amenities for the time, such as an on-site grocery store, bowling alley, and marina. The towers’ famous corn cob shapes make them instantly recognizable.

Resembling a giant armchair, Chicago’s 1929 Civic Opera House consists of a 45-story office tower flanked by two 22-story wings. The riverfront building boasts Art Deco ornamentation both inside and out and includes a performance space with 3,563 seats. The Civic Opera House is the second largest opera auditorium in the country behind New York’s Lincoln Center.

Completed in 1985, Chicago’s James R. Thompson Center has been polarizing since its inception. The Helmut Jahn-designed building sports a dramatic glass atrium as a nod to grand turn-of-the-century civic spaces like Union Station. Chicago’s most audacious postmodern building is also one of its most endangered. Deteriorating and facing a deferred maintenance bill of hundreds of millions of dollars, the state-owned Thompson Center has been eyed for redevelopment by Illinois lawmakers who are moving forward with a plan to sell the structure.

The original design was by the legendary firm of Burnham & Root from the 1880s and an interior lobby renovation was then executed by Frank Lloyd Wright in 1905. This early skyscraper is notable not only for its architectural pedigree, but also for being the oldest surviving high-rise in Chicago. Take a tour with the Chicago Architecture Center and get a glimpse of the landmark’s 11th-floor architects’ library.

One of the oldest surviving concert halls in the downtown area, the gorgeous Auditorium Theater from Dankmar Adler and Louis Sullivan first opened in 1889. The venue has played an important role in Chicago’s cultural history serving as home to both the Chicago Symphony Orchestra and the Civic Opera. Roosevelt University owns the theater and rescued it from decay.

The Field Museum traces its roots back to the Columbian Exhibition of 1893, when its collection was on display for visitors in Jackson Park. Marshall Field donated $1 million to house the collection in a permanent Neoclassical building in Grant Park in 1921. Only a fraction of the museum’s 40 million objects are on display—the most iconic being SUE the T. Rex, who just moved to a new space within the museum. Stanley Field Hall has a few new residents too: a flock of flying reptiles, a 122-foot long titanosaur, and floating plants.

One of the most visible neighborhood markers in Chicago’s Chinatown neighborhood, the Chinese-inspired gateway at the intersection of Wentworth and Cermak frames one of the area’s most busy commercial corridors. Designed by architect Peter Fung and installed in 1975, the structure draws inspiration from a wall in Beijing. The letters near the top of the gate translate to “the world belongs to the commonwealth,” a famous saying in early 20th century China.

Housing the Illinois Institute of Technology’s College of Architecture, S. R. Crown Hall is considered a masterpiece work by the father of modernism Ludwig Mies van der Rohe. The rectangular steel and glass structure embodies the designer’s “less is more” philosophy and was described by Mies as his “cleanest structure.” After its most recent renovation, Crown Hall looks as fresh as when it was completed in 1956.

This field house with Georgian and Tudor details is situated at the center of a 219-acre park named for the naturalist Alexander von Humboldt. It was designed in 1928 by Norwegian firm of Michaelsen & Rognstad and has intricately designed event spaces with terrazzo flooring and beautiful plaster ceilings.

Wrigley Field is nothing short of a Chicago institution. Built in 1914 by architect Zachary Taylor Davis who served as a draftsman for the legendary Louis Sullivan, the classic ballpark offers a unique throwback to a bygone age of baseball. The grittiness that used to exist around the stadium has been replaced by a new hotel, restaurants, and a grassy plaza known as Gallagher Way, but there’s plenty of nostalgia left once inside the Friendly Confines.

Designed by architect Benjamin Marshall, the 1928 Edgewater Beach Apartments is one of the North Side neighborhood’s most recognizable buildings. Clad in an unmistakable shade of “sunset pink,” the structure originally connected to the now-demolished 1918 Edgewater Beach Hotel. The surviving apartment building overlooks Lake Michigan at the north end of Lake Shore Drive.

Plans for this 4.5-acre horticultural oasis began in 1905 with the lofty goal of creating the world’s largest publicly owned conservatory under one roof. Taking design inspiration from the Midwest’s rural haystacks, famed Danish-American landscape designer Jens Jensen teamed with architects Schmidt, Garden, & Martin and engineers from Hitchings and Company to build a structure that was both sturdy and an elegant expression of the newly emerging Prairie School style. Since opening in 1908, the Garfield Park Conservatory has impressed both visitors and Chicago residents alike with its six greenhouses and two exhibition halls.

Established in 1865, the Union Stockyard was instrumental to the city’s rise to become the center of the American meatpacking industry and “hog butcher for the world.” While the sprawling stockyard once encompassed 475 acres of holding pens and railroad tracks, a 1934 fire destroyed nearly 90 percent of the complex. Today, Union’s iconic 19th-century limestone gate is the most visible remaining relic from Chicago’s meatpacking heyday.

Originally built as the South Shore Country Club, this South Side icon was penned by architects Marshall and Fox in 1905. Purchased by the Chicago Park District in 1975 and renamed as the South Shore Cultural Center, the landmarked Mediterranean Revival building features painstakingly restored historic details, a grandiose ballroom, and golf course. It remains a popular venue for weddings and other large events. Film buffs might recognize the exterior as the fictional “Palace Hotel Ballroom on Lake Wazzapamani” from the climax of The Blues Brothers.

Located on Chicago’s Far South Side, Pullman was the site of the country’s first planned industrial community in 1880. Conceived by railroad car tycoon George Pullman, the former company town is famous not only for the Romanesque architecture of its 1880 Clock Tower and Administration Building, but also the role it played in Chicago’s labor and civil rights movements. Pullman’s historic district was declared Chicago’s first—and only—National Monument in 2015.

Though technically outside of Chicago’s city limits in Oak Park, Illinois, the Frank Lloyd Wright Home and Studio is arguably one of the area’s most famous and influential of Wright’s buildings. Built in 1889, the structure on Chicago Avenue served as Wright’s personal home and design studio where a whole generation of architects honed and refined the iconic Prairie School style. Today, the Frank Lloyd Wright Trust manages and maintains the property as a museum.