A historic Chinese-American neighborhood on the South Side known for its pagoda-topped gate, dim sum restaurants, and the Chinatown Square shopping plaza along Wentworth Ave.

North America's largest convention center, hosting major trade shows and conventions on the lakefront just south of downtown.

A peninsula (once an island) on Lake Michigan, now a nature park and outdoor concert venue (Huntington Bank Pavilion), just south of the Museum Campus.

Home of the Chicago Bears NFL team, a lakefront stadium known for its distinctive blend of a classical colonnade and a modern glass-and-steel bowl.

One of the world's largest natural history museums, home to Sue, the largest and most complete T. rex fossil ever found.

America's first planetarium, offering space science exhibits and sky shows on the shore of Lake Michigan.

One of the five Great Lakes, forming Chicago's eastern border and defining much of the city's identity and skyline views.

Chicago's "front yard" is a sprawling downtown park hosting Lollapalooza, the Taste of Chicago, and other major events.

Anish Kapoor's reflective stainless-steel sculpture in Millennium Park is one of the city's most photographed landmarks.

The scenic roadway running along Lake Michigan's shoreline connects the city's lakefront parks, beaches, and skyline views.

A luxury hotel and residential skyscraper on the Chicago River, one of the tallest buildings in the U.S. designed by Jeanne Gang.

A historic pier turned entertainment destination with a Ferris wheel, restaurants, shops, and lake cruises.

The upscale stretch of North Michigan Avenue is lined with flagship stores, hotels, and skyscrapers.

A lively lakefront beach near Lincoln Park, known for its ship-shaped boathouse and volleyball courts.

Chicago's largest park, stretching along the lakefront and home to the zoo, conservatory, and numerous trails.

A free, historic zoo within Lincoln Park, one of the oldest zoos in the country.

Once the tallest building in the world, this downtown skyscraper still anchors Chicago's skyline and offers the Skydeck observation experience.

The observation deck near the top of the John Hancock Center (875 N. Michigan Ave.), offering panoramic views of the city and Lake Michigan from the 94th floor, plus TILT, an attraction that tilts visitors out over the edge of the building.

A distinctive black steel skyscraper on the Magnificent Mile, instantly recognizable by its X-braced exterior trusses; once the tallest building in Chicago, it offers the 360 CHICAGO observation deck near the top with sweeping views of the lake and city.

One of the oldest and largest art museums in the U.S., located in Grant Park; famous for its Impressionist collection, American Gothic, and the bronze lion statues guarding its main entrance.

A modern arena near McCormick Place on the South Side, home to DePaul University basketball and a venue for concerts and sporting events.

A grand Beaux-Arts fountain in Grant Park, one of the largest in the world, known for its color-lit evening water shows in summer; modeled after a fountain at Versailles.

A landmark vertical shopping mall and mixed-use tower on North Michigan Avenue, named for the historic Chicago Water Tower across the street; one of the first major urban shopping centers in the U.S., with retail, dining, and residences in a single skyscraper.

Located in Lincoln Park, this museum chronicles the city's history from its founding through the Great Chicago Fire, the World's Fairs, and beyond, with artifacts, photographs, and exhibits on Chicago's people and neighborhoods.

A prestigious private research university in the Hyde Park neighborhood, known for its Gothic-style campus, rigorous academics, and ties to dozens of Nobel laureates; its main quadrangles and Rockefeller Memorial Chapel are landmarks in their own right.

The presidential library component housed within the Obama Presidential Center in Jackson Park, chronicling Barack Obama's life and presidency, is part of the broader campus that also includes a Chicago Public Library branch and museum, which opened to the public on June 19, 2026.

Housed in the former Palace of Fine Arts from the 1893 World's Fair, this Hyde Park museum features hands-on science exhibits, a real U-505 German submarine, and an Omnimax theater.

A popular lakefront beach on Chicago's North Side, known for its dunes (a rare natural habitat for the endangered piping plover), a harbor, and views back toward the downtown skyline.