How to get an insider tour of Chicago and its celebrated architecture

If urban legend is to be believed, the world was forever changed on a dry, windy Chicago evening on 8 October 1871 by a cow called Daisy. She knocked over a lantern, causing one of the largest urban fires in modern history. Around 3.5sq miles of the Illinois city burned down, destroying more than 17,000 buildings and leaving a blank canvas for new architectural styles and groundbreaking engineering.

The rebuild began almost instantly and, by 1885, Chicago had enshrined itself in architectural history as the home of the world’s first skyscraper, the Home Insurance Building. Boat tours on the Chicago River look at the history of the city’s skyline, but new walks from Inside Chicago aim to reveal a different perspective. “Everyone comes to Chicago and does the boat tour and it’s great,” says founder and guide Hillary Marzec, “but they miss what’s in the belly of the beast, so to speak.” Her team takes travellers on a whirlwind walking tour of the Loop — the downtown district — providing access to five famous spaces that give context to the architectural marvels visitors see on the streets of the city.

The tours have launched in time for the 140th anniversary of the Home Insurance Building in 2025, which was torn down in 1931 to make way for larger buildings. Walks knit together different architectural and interior design periods, from the streamlined and futuristic art deco Chicago Board of Trade building to the postmodern architecture of Federal Plaza. At The Rookery, built in the late 1880s, travellers get to see the lobby that was re-designed by Frank Lloyd Wright in 1905 and inspired later buildings in Chicago.

“Architecture is what makes a city,” Hillary points out. “The buildings are talking to each other here. As soon as you understand the references, it’s like you’re in on the joke, too, and Chicago is the one place where you really want to be a part of the conversation.”