Chicago

The most celebrated restaurant in America — and one of the great restaurants in the world. Chef Grant Achatz's multi-course tasting menu is the most technically ambitious and emotionally resonant cooking in the country: edible balloons, tableside desserts painted directly onto the table, and dishes that dissolve the boundary between food and art. Book three months in advance. The Gallery experience (the most theatrical) requires the most lead time.

Chef John Shields and Karen Urie Shields have built one of the most quietly extraordinary restaurants in America — a two-Michelin-star tasting menu in the West Loop that draws on the finest Midwestern ingredients with a restraint and intelligence that is the antithesis of Alinea's theatrics. The two restaurants represent the full range of what contemporary American fine dining can be.

Chef Stephanie Izard's flagship restaurant is the most reliably excellent large-format dining experience in Chicago — a boisterous, generous, endlessly creative menu of share plates that draws on global influences without losing its Midwestern roots. The wood-roasted pig face, the goat liver mousse, and the sautéed green beans are the essential dishes.

The finest deep-dish pizza in Chicago — and the most hotly contested title in the city. Lou Malnati's buttery, flaky crust, its layer of sausage, its blanket of mozzarella, and its chunky tomato sauce on top is the definitive version of the form. Order the Malnati Chicago Classic; allow 45 minutes for it to bake; eat it with a fork.

The most atmospheric steakhouse in Chicago — a dimly lit, jazz-soundtracked room in River North that serves the finest dry-aged steaks in the city alongside exceptional oysters, a magnificent wine list, and a cocktail programme that is among the best in Chicago. The bone-in ribeye is the essential order.

The most famous burger in America — a double smash patty with American cheese, dijonnaise, and a fried egg on a brioche bun, served in a diner that has been packed since the day it opened. The wait can be long; it is always worth it. Order the bone marrow as a starter.

The Chicago Architecture Center Boat Tour

The finest 90 minutes in any American city — a narrated cruise along the Chicago River that reveals the most extraordinary collection of 20th-century architecture in the world. The guides are exceptional; the views of the skyscrapers from the water are unlike anything you can see from the street. Book the evening cruise in summer for the most dramatic light.

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 (Seurat's A Sunday on La Grande Jatte, Picasso's The Old Guitarist, Hopper's Nighthawks), a superb collection of American art, and the Thorne Miniature Rooms. Allow a full day; the Modern Wing alone requires three hours.

Millennium Park — Morning

Arrive at Millennium Park before 9am, when the crowds are thin and the light on Cloud Gate is extraordinary. Walk to the Jay Pritzker Pavilion, cross the BP Bridge to Maggie Daley Park, and end at the lakefront. The view of the skyline from the lakefront path, with the park in the foreground and the towers behind, is the finest urban panorama in America.

Buddy Guy's Legends

The most important blues club in America — owned and occasionally performed in by Buddy Guy, the last living link to the original Chicago blues scene. The house band plays every night; Buddy Guy himself performs in January. The venue is unpretentious, the music is extraordinary, and the experience of hearing electric blues in the city that invented it is irreplaceable.