After the Great Fire of 1871 burned the heart of Chicago to the ground, the city rebuilt itself taller, faster and bolder than anywhere else in the world, and in the process it gave the world the skyscraper. This walk tells that story in the Loop, the downtown ringed by the elevated train tracks. It starts under a Tiffany glass dome at the Chicago Cultural Center, crosses Millennium Park to the Bean and the Art Institute, then heads into the canyons of the financial district for the buildings that changed how cities are built, before finishing beneath the lights of the Chicago Theatre on State Street. It runs about 3.4 kilometers, a little over two miles, and it is the best of our self-guided walking tours for anyone who wants to understand why Chicago looks the way it does.

Before you set off

Give it two to three hours at an easy pace, longer if you get lost in the Art Institute, which is very easy to do. The route is completely flat and paved, but the streets are busy, so expect lots of crossings and crowds at lunchtime. A weekday is best, because several stops are working office lobbies that are open during business hours and quieter or closed at weekends, so check before you go. Chicago weather is famously changeable. The wind funnels between the towers and can be bitter in winter, so bring a warm layer even on a mild day, and in summer the open plazas get hot while the narrow streets stay in shade. You will spend much of this walk looking up, which is the point, but watch the curbs. For most of the way you will hear the elevated trains rattling overhead on their tracks around the Loop, which have circled downtown since the 1890s and are part of the soundtrack. The Art Institute charges admission, and the rest of the route is free.

Chicago Cultural Center

Step inside and climb the grand staircase to Preston Bradley Hall, then stand in the middle of the room and look straight up. Above you is a dome of Tiffany glass, thirty-eight feet across and made of some thirty thousand pieces, and it is said to be the largest Tiffany glass dome in the world. This building opened in 1897 as the city's first central public library, and the library itself was born out of disaster. When the Great Fire destroyed Chicago in 1871, people in Britain decided to help the city rebuild its mind as well as its streets. The author Thomas Hughes and others gathered thousands of donated books and shipped them across the Atlantic, reportedly with Queen Victoria herself among the donors, and those gifts became the seed of the Chicago Public Library. Look at the walls of the staircases and you will see mosaics of glass and marble spelling out quotations about books in several languages. The library moved out decades ago and the building now hosts free exhibitions, concerts and events, with a second, Renaissance-style glass dome over the hall at the north end. When you are ready, leave by the Michigan Avenue doors, cross the avenue at Washington Street into Millennium Park, and in about four minutes you will see a giant silver shape on the plaza ahead.

Cloud Gate

Walk all the way around it, then underneath it. Cloud Gate, which everyone in Chicago calls the Bean, was designed by the British artist Anish Kapoor, who has said he was inspired by liquid mercury. It is made of 168 stainless steel plates, welded together and polished until the seams vanished, so the whole thing looks like one drop of silver that has landed on the plaza. It weighs about 110 tons. Stand back and see how it bends the skyline of Michigan Avenue into a curve, then walk under the arch, into the hollow the artist calls the omphalos, the navel, where your reflection multiplies and twists above your head. Kapoor reportedly was not fond of the nickname, but the city never listened. Millennium Park itself is a small marvel of engineering. Until the late 1990s, this corner was an ugly stretch of railway tracks and parking lots, and the park was built over the top of them, opening in 2004, years behind schedule and well over budget. Today it is one of the most popular places in the city, with Frank Gehry's steel band shell just to the north. Head south through the park, past the two glass towers of the Crown Fountain, where faces of Chicagoans appear on giant screens and spit water. Cross Monroe Street and keep south along Michigan Avenue for about five minutes to a pair of bronze lions.

Art Institute of Chicago

Cloud Gate Chicago Stand at the bottom of the steps between the two bronze lions. Sculpted by Edward Kemeys, they have guarded this door since 1894, and the city treats them like family: at Christmas they wear wreaths, and when the Blackhawks won the Stanley Cup they got giant hockey helmets. The building behind them was put up for the World's Columbian Exposition of 1893, the great fair that showed off the rebuilt city to the world, and was designed by the same firm as the Cultural Center you just left. Inside is one of the great art collections on earth. Two of the most famous American paintings hang here. One is Grant Wood's American Gothic, the stern farmer with a pitchfork and the woman beside him, for which Wood's sister and his dentist posed. The other is Edward Hopper's Nighthawks, with its lonely figures in an all-night diner, painted in 1942 and bought by the museum that same year. Seurat's huge dotted painting of Parisians in a park, A Sunday on La Grande Jatte, is here too, and it is even more astonishing in person. If you plan to come back for a proper visit, carry on for now. Go one block south to Jackson Boulevard, turn right and walk west, under the elevated tracks on Wabash Avenue and across State Street. In about eight minutes, at Dearborn Street, look for a dark, plain building on the left.