There is a moment on the Chicago Architecture Boat Tour — somewhere between the Tribune Tower and the Wrigley Building — when you understand that Chicago is not merely a great American city. It is the great American city.
Chicago does not ask for your approval. It has the tallest buildings, the best deep-dish pizza, the most important jazz and blues legacy in the world, and a waterfront that would make any European city weep with envy. The Riverwalk runs along the south bank of the Chicago River from Lake Shore Drive to Lake Street — a mile-and-a-half of waterfront promenade lined with restaurants, bars, kayak rentals, and the kind of architectural spectacle that makes you stop every thirty seconds to look up.
The Architecture Boat Tour departs from the Riverwalk and runs ninety minutes along the river and out into Lake Michigan. Chicago Architecture Center runs the most comprehensive version, and it is worth every penny. The guides are extraordinary — part historian, part comedian, part architectural evangelist — and by the time you disembark you will have a working knowledge of the Chicago School, the Prairie Style, and why Mies van der Rohe's Seagram Building in New York is actually a Chicago idea transplanted to Manhattan.
The Loop anchors the city's downtown, a grid of elevated train tracks, glass towers, and some of the most important public art in the world. Millennium Park anchors the south end, and Cloud Gate — the giant reflective bean sculpture that every tourist photographs and every Chicagoan secretly loves — is genuinely one of the great public artworks of the twenty-first century.
"The deep-dish at Lou Malnati's is worth the flight. The Green Mill on a Tuesday night is worth the flight. Put them together and you have one of the great days on earth."
Chicago's food culture is one of the most underrated in the world. The West Loop neighbourhood has become one of the most exciting restaurant districts in the United States, with Randolph Street housing everything from Michelin-starred tasting menus to the best Korean fried chicken you will ever eat. For deep-dish, Lou Malnati's on Wells Street in the Gold Coast is the gold standard — a buttery, flaky crust filled with sausage, cheese, and a thick layer of chunky tomato sauce applied on top. The pizza takes forty-five minutes to bake, which gives you time to drink a beer and be right about everything.
The Cocktail Scene
The Violet Hour in Wicker Park is one of the best cocktail bars in the United States — a beautiful, dimly lit room with no sign on the door and a menu of original cocktails that changes seasonally. The Aviary in the West Loop, Grant Achatz's cocktail laboratory, is the most technically ambitious bar in the city, where drinks arrive in custom glassware and occasionally in ice spheres that melt to reveal their contents. For something more neighbourhood and less theatrical, the Long Room on Irving Park Road in Lakeview is a perfect Chicago bar — dark wood, good whiskey, and a jukebox that skews heavily toward the Replacements and Wilco.
For Italian beef — Chicago's other great sandwich — Al's Beef on Taylor Street in Little Italy is the original, and the combination of slow-roasted beef, giardiniera, and sweet peppers on a Turano roll is one of the great sandwiches of civilisation. The coffee scene is equally serious: Intelligentsia Coffee pioneered the third-wave movement here, and their Monadnock Building location in the Loop is the perfect pre-architecture-tour stop.
The Blues, the Jazz, and the Green Mill
Chicago's musical legacy is inseparable from its history. The Great Migration brought hundreds of thousands of African Americans from the Deep South to Chicago, and with them came the Delta blues, which transformed in the city's electric clubs into the Chicago Blues — louder, more urban, more electrified. Muddy Waters, Howlin' Wolf, Buddy Guy, and Junior Wells all made their names here.
Buddy Guy's Legends on South Wabash is the essential Chicago blues club — Buddy himself still plays there regularly. The Green Mill in Uptown is the city's great jazz club, a 1907 speakeasy that Al Capone used to frequent and that still hosts live jazz seven nights a week. The room has barely changed in a century, and on a good night, with a Manhattan in hand and a quartet working through a Coltrane standard, it is one of the most atmospheric rooms in America.
Chicago in Frame
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Gerald's Scorecard
Chicago, Illinois, USA
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Gerald's Final Word
I came to Chicago expecting a great American city. I left understanding that it might be the great American city — the one that best embodies the country's ambition, its contradictions, its extraordinary capacity for reinvention. The Architecture Boat Tour alone is worth the flight. The deep-dish at Lou Malnati's is worth the flight. The Green Mill on a Tuesday night, with a quartet playing Monk and a Manhattan that costs twelve dollars, is worth the flight. Put them all together and you have one of the great days on earth.
Best Day Ever.
— Gerald Shaffer, March 2026