"Chicago is the most underestimated great city in America — and the one that rewards the traveller who arrives with genuine curiosity."
Chicago sits on the southwestern shore of Lake Michigan — a freshwater sea so vast it has its own weather, its own tides, and its own horizon. The city rebuilt itself from nothing after the Great Fire of 1871 and in doing so created the most extraordinary collection of modern architecture in the world: the first skyscraper, the first steel-frame building, the first curtain-wall tower. The dining scene — anchored by Alinea, one of the most celebrated restaurants on earth, and a deep tradition of steakhouses, Italian beef, and deep-dish pizza — is among the finest in the country. The blues and jazz heritage is irreplaceable. And the lakefront, with its 26 miles of public beaches and parks, is the finest urban waterfront in America.
"The Architecture Boat Tour — the finest 90 minutes in any American city."
TastesOf Editorial
At a Glance
What Not to Miss
The Architecture Boat Tour
The finest way to understand Chicago — a 90-minute narrated cruise along the Chicago River and Lake Michigan that reveals the most extraordinary collection of 20th-century architecture in the world. The city built itself from scratch after the Great Fire of 1871 and invited every great architect of the modern era to do their finest work. The result is a skyline unlike any other on earth.
Millennium Park & Cloud Gate
The most visited public space in the Midwest — a 24.5-acre park in the heart of the Loop anchored by Anish Kapoor's Cloud Gate sculpture (universally known as "The Bean"), the Jay Pritzker Pavilion designed by Frank Gehry, and Jaume Plensa's Crown Fountain. Free, extraordinary, and essential.
The Art Institute of Chicago
One of the finest art museums in the world — with the greatest collection of Impressionist and Post-Impressionist paintings outside of Paris, a superb collection of American art, and the Thorne Miniature Rooms, which are among the most extraordinary objects in any museum anywhere. The Modern Wing, designed by Renzo Piano, is a masterpiece of museum architecture.
The Chicago Blues Scene
Chicago is the home of electric blues — the city where Muddy Waters, Howlin' Wolf, and Buddy Guy transformed the Delta blues into the music that gave birth to rock and roll. Buddy Guy's Legends on South Wabash is the essential venue; the Chicago Blues Festival in June is the finest free music festival in America.
Deep-Dish Pizza — The Original
Chicago's most famous culinary contribution to the world — a thick, buttery crust filled with cheese, toppings, and a chunky tomato sauce on top. Lou Malnati's, Giordano's, and Pequod's are the three great institutions; the debate over which is finest is the most passionate civic argument in Chicago.
The 606 Trail
Chicago's answer to New York's High Line — a 2.7-mile elevated trail built on a disused railway line through the Wicker Park, Bucktown, and Logan Square neighbourhoods. The trail is the finest way to experience Chicago's most creative and dynamic residential neighbourhoods, and the street art along the route is exceptional.
Where to Stay
The Peninsula Chicago
LuxuryThe finest hotel in Chicago — on Michigan Avenue at the corner of Superior Street, with views of the Magnificent Mile and Lake Michigan, a world-class spa, and a restaurant programme that is among the best in the city. The afternoon tea in the lobby is the finest in Chicago.
Soho House Chicago
Design BoutiqueThe most stylish hotel in Chicago — a beautifully converted red-brick warehouse in the Fulton Market District, the city's most dynamic neighbourhood. The rooftop pool is the finest in the city; the restaurant is excellent; and the location, surrounded by the best new restaurants in Chicago, is unbeatable.
The Langham Chicago
River ViewsA spectacular hotel in the former IBM Building designed by Mies van der Rohe — with floor-to-ceiling windows overlooking the Chicago River, the most beautiful indoor pool in the city, and a location in the heart of the Loop that is ideal for exploring the architecture and the museums.
The Verdict
Take the architecture boat tour, eat at Alinea, get deep-dish at Lou Malnati's, and spend a night at Buddy Guy's Legends. Chicago will not disappoint.