Chicago

Chicago has a chip on its shoulder about New York and Los Angeles, and the chip produces better results than either coast might expect. The architecture is more consistently interesting than New York’s. The food is more varied and honest than the celebrity-chef showcase that LA can become. The music traditions – blues, house, jazz, gospel – are native in a way that cannot be manufactured for visitors. The city is also genuinely affordable relative to the coasts, which is a fact that Chicagoans mention fairly often and that turns out to be true.

The Architecture River Cruise

If you do one thing in Chicago, make it the Chicago Architecture Center’s river cruise – voted the number one boat tour in the United States by USA Today readers in 2025. Led by trained docent volunteers, 90 minutes on the Chicago River with commentary on the buildings that make the city’s skyline what it is: the Tribune Tower, the Wrigley Building, Mies van der Rohe’s glass towers, the Corncob buildings, and the 1893 Chicago Architecture’s revival of the neoclassical. Chicago invented the skyscraper, refined it, and the river gives you the best view of the argument.

The Museums and Parks

The Art Institute of Chicago on Michigan Avenue holds over 300,000 works. The Impressionist collection rivals Parisian museums; Grant Wood’s American Gothic and Seurat’s A Sunday on La Grande Jatte are both here. Allow three hours minimum; free guided tours depart regularly.

Millennium Park, directly behind the Art Institute, contains Cloud Gate (the Bean) – 110 tons of polished stainless steel in a bean shape, with the city skyline reflected and distorted across its surface. Go early morning when the park is less crowded.

Willis Tower’s Ledge – a glass platform extending 4.3 feet beyond the building’s exterior, 103 stories above Michigan Avenue – is one of the few tourist experiences in Chicago that genuinely unsettles visitors who thought they were comfortable with heights.

The Field Museum (natural history), Shedd Aquarium, and the Art Institute form a Museum Campus cluster near the lakefront in Grant Park. Plan a full day for two or an extraordinary amount of time for all three.

Food

Deep-dish pizza is the city’s signature and Giordano’s and Lou Malnati’s are the proper addresses. A Chicago-style hot dog requires mustard, yellow onions, bright green relish, tomato wedges, dill pickle, sport peppers, and celery salt – never ketchup. The rule exists and is enforced by social pressure rather than law. The West Loop restaurant district has evolved into one of the best eating destinations in the United States since around 2015, with a concentration of serious cooking in a small area.

Music

Chicago’s South Side birthed the electric blues and the tradition survives at Buddy Guy’s Legends and Kingston Mines. The Green Mill Cocktail Lounge in Uptown is a 1907 jazz club with preserved interior and live music seven nights a week. House music was invented in Chicago in the early 1980s at the Warehouse club; the genre is named after it.

Getting Around

The L (elevated rail) is the fastest way to cover the city. Get a Ventra card for unlimited rides. Lines are colour-coded. The lakefront is free, flat, and well-maintained for cycling and walking.