Chicago

Chicago is where the skyscraper was born, and architecture is the reason to come. The classic first move is an architecture river cruise — ninety minutes along the three branches of the Chicago River, narrated by guides who can read a century and a half of building from the water: the terracotta Wrigley Building and Gothic Tribune Tower, Mies van der Rohe's glass boxes, Marina City's “corncobs”, and the black tapered shaft of the Willis (formerly Sears) Tower, whose glass-floored Skydeck ledges out 1,353 feet above the Loop. On foot, the Loop itself is an open-air museum: Sullivan's ornamented Carson Pirie Scott store, the Rookery with Frank Lloyd Wright's light-filled lobby, the Chicago Cultural Center's Tiffany dome. The Chicago Architecture Center runs the definitive walking tours. For Wright specifically, the suburb of Oak Park holds his home, studio and the Unity Temple within an easy ride on the Green Line.

Chicago's eighteen miles of lakefront are entirely public — beaches, harbours, a continuous bike-and-run path, and a string of parks that hold many of the city's headline sights. Millennium Park is the centrepiece: Anish Kapoor's mirrored Cloud Gate, the Crown Fountain's projected faces, and Frank Gehry's Pritzker Pavilion, which hosts free summer concerts on the Great Lawn. Next door, the Art Institute of Chicago is one of the world's great museums — Seurat's A Sunday on La Grande Jatte, Hopper's Nighthawks, Grant Wood's American Gothic and a sweep of Impressionism to rival Paris. South along the lake, the Museum Campus gathers the Field Museum of natural history (home of Sue the T. rex), the Shedd Aquarium and the Adler Planetarium on a peninsula with the best downtown skyline view in the city. The Museum of Science and Industry, further south in Hyde Park, fills a Beaux-Arts palace left from the 1893 World's Fair.

Downtown is only the beginning; Chicago is a city of ninety-odd neighbourhoods, and the character lives in them. Chicago blues — electrified by the Great Migration from the Mississippi Delta — still plays nightly at clubs like Buddy Guy's Legends and Kingston Mines, and the gospel and house-music traditions run just as deep. Pilsen on the Lower West Side is the Mexican-American heart of the city, its walls covered in murals and the National Museum of Mexican Art free to enter. Wicker Park and Logan Square hold the indie music venues, vintage shops and a restaurant scene that rivals downtown's. Along the lake, Lincoln Park pairs a free zoo and conservatory with leafy streets, while the Gold Coast keeps the city's gilded-age mansions. Sport is a religion here: Wrigley Field, the ivy-walled 1914 ballpark of the Cubs in the neighbourhood that takes its name, is worth a game or a tour whatever the standings.

The clichés are real and worth doing once: deep-dish pizza — a buttery crust holding a deep layer of cheese under chunky tomato, baked at Pizzeria Uno, Lou Malnati's or Pequod's with its caramelised crust — and the Chicago-style hot dog, dragged through the garden (mustard, relish, onion, tomato, pickle, sport peppers, celery salt) and never, ever ketchup. But the city's eating runs far deeper. The Italian beef sandwich, the tavern-cut thin pizza locals actually eat midweek, and the immigrant cooking of Devon Avenue (South Asian), Argyle Street (Vietnamese) and Pilsen (Mexican) are the everyday pleasures. At the top end, Chicago holds one of America's most serious fine-dining scenes — Alinea among the world's most influential restaurants — and a deep bench of neighbourhood chefs. The historic French Market and the Time Out Market gather it under one roof for the time-pressed.

Chicago is flat, gridded and walkable downtown, and the CTA “L” (the elevated and subway network) plus buses reach everywhere a visitor needs, including both airports — the Blue Line to O'Hare (ORD) and the Orange Line to Midway (MDW). A Ventra card or a contactless tap covers it all. Divvy bike-share and the lakefront trail make cycling a genuine way to sightsee in warm months. Timing matters more here than in most American cities: summer (June–September) is Chicago at its peak — beaches open, rooftops busy, and a near-continuous run of mostly free festivals along the lake, from Blues Fest to the air and water show. Autumn is crisp and clear; spring is unpredictable. Winter is real Midwestern cold with lake-effect wind, but the museums, the Christkindlmarket and a quieter city reward the well-dressed visitor.