Standing on the Chicago Riverwalk, your eyes naturally gravitate to the towering architectural gems along the Chicago River: the gleaming Wrigley over the movable bridge, the twin “corn cobs” of Marina City, and more. But the beginnings of Chicago’s greatness can actually be found … under your feet! The pieces of metal embedded in the pavement mark the edge of a fortress that stood decades before Chicago’s founding in 1833: the outpost called Fort Dearborn.

Imagine you’re standing here as dawn breaks on the morning of July 24th, 1915. You’re surrounded by thousands of excited fellow factory workers from the Western Electric Company, all dressed up and waiting to board one of several huge steamers docked on the river. You’re anxious to get on the boat and head to the day’s event: a company picnic in the Indiana Dunes across Lake Michigan. But you never make it.

Chicagoans simply call the iconic artwork in Daley Plaza “The Picasso,” after its famous Spanish creator, Pablo Picasso. He didn't name the piece, and no one really knows what he intended it to represent.

Before cell phones and text messaging, Chicagoans planning to rendezvous city centre traditionally met right here, under the first of two great clocks at the historic Marshall Field & Company department store. Many travelled here—and still do—via the city’s iconic elevated train, known locally as the “el.” In fact, a ramp from the Wabash Street stop leads right into the store.

The towering building of the Chicago Board of Trade looms at the southern end of what Chicagoans call the LaSalle Street “canyon” because of the narrow corridor lined on both sides by tall, close-set buildings. If you’ve never been to Chicago, you may still recognise this street and this building, as both have been featured in many popular films.

Where can you find one of the world’s first skyscrapers? Right here! At eleven stories tall, the Rookery was the tallest building in the world when it was completed, but it was the ingenious steel frame design that made today’s towering skyscrapers possible. This technique is one of the hallmarks of the first “Chicago School” of architecture, which provided the foundation—no pun intended, well actually, it was intended—for the development of modern cityscapes.

Who could miss the eye-popping 53-foot “Flamingo” sculpture gracing the sleek space at Chicago’s Federal Plaza? It was created by American artist Alexander Calder. This plaza flanks Chicago’s Federal Centre, a grouping of three glass-and-steel federal government buildings: the Dirksen Building, the Kluczynski Building, and the Loop Station of the United States Post Office.

Chicago’s Buckingham Fountain is the magnetic hub of Grant Park, what’s known as “Chicago’s Front Yard.” At 150 vertical feet, it’s one of the largest fountains in the world! Inspired by the Latona Fountain at the Palace of Versailles, in France, its design represents Lake Michigan. Its four horses symbolise the four states that border the lake. One and a half million gallons of water circulate through the fountain, supplying hourly water shows from May to October. If you’re here at night, you’ll enjoy thrilling light displays during those months or thousands of twinkling lights in the winter.

The Art Institute of Chicago is one of the world’s most revered art museums. Be sure to take a selfie with one of its iconic bronze lions. Self-taught 19th-century sculptor Edward Kemeys created these lions. Kemeys was the first professional American animalier. That’s an artist who exclusively sculpts realistic-looking animals. To hone his craft, he left his home in New York and went west to observe animals in the wild, living with Native American tribes and travelling with fur trappers. When Kemeys later came here to Chicago, the Art Institute invited him to show his work. His beloved beasts have watched over the Boul Mich since 1894.