Beyond the Loop

The only remaining structure from the Union Stock Yards, once the largest meatpacking complex in the world (1865-1971). This neo-gothic limestone gate from 1877 is the sole survivor of an industrial empire that defined Chicago. At its peak, the stockyards processed 18 million animals annually. Upton Sinclair wrote The Jungle about conditions here. The smell could be detected miles away. Now: one ornate gate standing alone on Exchange Avenue, a National Historic Landmark marking an industry that no longer exists. Behind the gate: industrial lots, some new development, and the absence of what was once the economic engine of the Midwest.

Scattered throughout Jackson Park: original arc lamp posts designed by Charles Atwood, Westinghouse manhole covers fabricated for the fair, the Wooded Island's Japanese garden on the site of the Phoenix Pavilion, and the Columbia Stone Pedestrian Bridge. The 1893 World's Columbian Exposition was demolished after the fair — almost everything burned or was torn down. These fragments are what remains of the "White City" that introduced Ferris wheels, Cracker Jack, and electric lighting on a scale never seen before. Most visitors to Jackson Park walk past 130-year-old infrastructure without realizing they're treading on World's Fair history.

A 1929 movie palace that never stopped showing films, preserving the experience of watching a movie in an ornate atmospheric theater. The ceiling is painted to look like a night sky with twinkling stars and moving clouds. The organ still rises from the orchestra pit for special screenings. The Music Box programs classics, cult films, foreign cinema, and midnight movies — this is where you watch The Room with 200 people shouting at the screen, or catch a 35mm print of a Hitchcock film. The theater has been lovingly maintained, which means it feels like 1929 in the best possible way. Popcorn is fresh. The balcony is intact. Movies look better here.

The actual location where FBI agents shot John Dillinger on July 22, 1934, after he watched a movie. The theater on Lincoln Avenue still stands, now operating as a live venue. A historical marker notes the spot where "Public Enemy No. 1" died. The movie he watched: Manhattan Melodrama. The woman who tipped off the FBI (the "Lady in Red") was actually wearing orange. Dillinger walked out of this theater into an ambush that's now Chicago crime folklore. The building has been renovated, but standing outside the former theater entrance connects you to a specific moment when federal law enforcement killed a celebrity criminal on a Chicago street.

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The oldest jazz club in the United States, famous for its connections to Al Capone (his favorite booth is still there). It opened in 1907 as Pop Morse's Roadhouse. The interior is a preserved 1940s time capsule. Regulars know to bring cash and respect the music—silence is enforced during sets.

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The first planned industrial community in the United States, built by George Pullman for his employees. It was the site of the 1894 Pullman Strike which changed labor history. The Administration Clock Tower Building is the centerpiece of a neighborhood that feels frozen in the 19th century. Walking these streets explains the history of American labor unions better than any textbook.