Chicago

The Chicago River Architecture Boat Tour — Skyscrapers from the Water
The Chicago Architecture Center boat tour on the Chicago River is the single best way to experience Chicago's extraordinary architectural heritage — a 90-minute narrated cruise from Navy Pier west along the main branch of the Chicago River and its two branches, passing approximately 50 significant buildings spanning from the 1880s to the present, with expert architectural commentary from trained docents of the Chicago Architecture Foundation.

Lincoln Park, the Zoo, North Avenue Beach & Old Town
Lincoln Park — the 1,208-acre public park stretching 10 kilometres along Chicago's North Side lakefront — is the largest of Chicago's 580 parks and one of the most used urban parks in the United States, combining the Lincoln Park Zoo (the oldest free admission zoo in the United States), North Avenue Beach, the Lincoln Park Conservatory, and the neighbourhood of Old Town (one of Chicago's oldest and most distinctive residential areas).

Millennium Park, Art Institute & the Magnificent Mile
The stretch of Chicago's lakefront from Millennium Park to the Magnificent Mile constitutes the cultural and commercial spine of the city — from Cloud Gate and the Jay Pritzker Pavilion in the park, through the world-class collection of the Art Institute of Chicago, to the shopping and architecture of Michigan Avenue and the Chicago Riverwalk.

Bronzeville, Pullman & the African-American History of the South Side
The South Side of Chicago — the vast swath of the city south of the Loop, home to approximately 1 million residents — is the historic heart of African-American Chicago, the destination of the Great Migration (the movement of approximately 6 million African Americans from the rural South to northern cities between 1910 and 1970) and the birthplace of Chicago Blues, gospel music, and much of the cultural innovation that made Chicago one of the most creatively significant cities in 20th-century American history.

Hyde Park, the University of Chicago & Obama's South Side
Hyde Park — the lakefront neighbourhood on Chicago's South Side, 13 kilometres south of the Loop, home to the University of Chicago (founded 1890), the Museum of Science and Industry, and the presidential library of Barack Obama (scheduled to open 2025 as the Obama Presidential Center in Jackson Park) — is one of the most intellectually and culturally significant residential neighbourhoods in American urban history.

The Loop, Willis Tower & Chicago's Architectural Legacy
Chicago's Loop — the central business district enclosed within the elevated 'L' train tracks — is the birthplace of the modern skyscraper and the site of the most significant concentration of 20th-century American commercial architecture in the world, a continuous open-air museum of architectural innovation from the Chicago School of the 1880s-1900s through Mies van der Rohe's post-war Modernism to the structural innovations of Skidmore, Owings & Merrill.

Deep-Dish Pizza, Blues, Jazz & the Neighborhoods — Wicker Park to Pilsen
Chicago's cultural identity is as much defined by its food, music, and neighbourhood life as by its architecture: the deep-dish pizza invented by Ike Sewell at Pizzeria Uno in 1943, the Chicago blues tradition that transformed Southern Delta blues into the electrified urban sound that became rock and roll, and the neighbourhood diversity that makes Chicago a city of distinct ethnic and cultural enclaves from Wicker Park's artists to Pilsen's Mexican-American muralists.

Wrigley Field, Cubs Baseball & the Wrigleyville Neighborhood
Wrigley Field (1060 West Addison Street, Wrigleyville — the baseball stadium of the Chicago Cubs, opened in 1914 as Weeghman Park, renamed Cubs Park in 1920 and Wrigley Field in 1926 after chewing gum magnate William Wrigley Jr., the second-oldest Major League Baseball stadium in the United States after Fenway Park in Boston) is one of the most beloved sports venues in America and the centrepiece of one of Chicago's most distinctive and tourist-friendly neighbourhoods.

Museum Campus — Shedd Aquarium, Field Museum & Adler Planetarium
Museum Campus Chicago — the 57-acre peninsula extending into Lake Michigan immediately south of Grant Park, accessible by the lakefront trail and by bus — is the most concentrated collection of major natural history and science institutions in the United States, combining three world-class museums within walking distance of each other: the Field Museum (natural history), the Shedd Aquarium, and the Adler Planetarium.