Chicago

The Great Chicago Fire of October 1871 burned roughly three square miles of the city to the ground, destroying the young metropolis’s downtown almost entirely. What followed was not caution but a kind of architectural dare: rebuilt on the same grid, with fireproof construction and steel-frame ambition, Chicago spent the next half-century inventing the skyscraper and refusing to build small ever again. The city’s hotels are inseparable from that story — they are not merely places travelers slept, but declarations of how seriously Chicago intended to be taken.

The Palmer House opened just thirteen days before the 1871 fire and burned along with everything else; Potter Palmer rebuilt it immediately, and the version standing today, completed in 1927, carries that stubbornness in its scale. Its lobby, with twenty-one ceiling murals modeled on Versailles, was engineered to be the most extraordinary interior space an American hotel had ever attempted — a claim that still holds up. It was also, memorably, the birthplace of the brownie, invented in the hotel’s kitchen for the 1893 World’s Fair.

Up on Michigan Avenue at the edge of Lake Michigan, The Drake opened in 1920 as the deliberate exclamation point at the top of what would become the Magnificent Mile, built by a family determined to give Chicago a lakefront hotel equal to anything on the East Coast. A few blocks south on Michigan Avenue, the Congress Plaza Hotel rose in 1893 to house visitors to the World’s Columbian Exposition and has since witnessed a century of Chicago history unfold in its rooms, including one of the longest hotel labor strikes in American history, a ten-year standoff between 2003 and 2013 that became a defining chapter of the modern hospitality labor movement.

These three hotels, standing within walking distance of one another along the Loop and Michigan Avenue, trace the arc of Chicago’s confidence — from the ashes of 1871 through the Gilded Age and into the Jazz Age, each one built to answer the same question the fire first posed. For a deeper dive into what it’s actually like to stay in each one today, see our full guide at /blog/historic-hotels-chicago.