A Journey Through Chicago’s West Loop

Chicago’s West Loop tells the story of America’s first skyscraper city. On this walking tour, you’ll discover the iconic Art Deco towers and pioneering modernist structures that reflect the city’s evolution from a trading post to a global metropolis.

This tour starts at the French Market inside Ogilvie Train Station, an indoor marketplace inspired by European grocery stores. You’ll make your way past the imposing Boeing Building and along the Chicago River with its scenic waterfront views. You’ll walk through the financial district where you’ll encounter landmarks like the Willis Tower (formerly Sears Tower) and the Chicago Board of Trade, which has influenced global commerce since 1848.

As you continue, you’ll discover standout architecture like The Rookery – Chicago’s oldest surviving high-rise, featuring birds hidden throughout its design – and the Federal Plaza. You’ll hear about Chicago’s transformation after the Great Fire of 1871 and how it became a center for architectural innovation. The tour ends at the magnificent Buckingham Fountain in Grant Park.

During this two-hour walking tour, you’ll have a chance to:

• Visit historic Art Deco masterpieces like the Civic Opera Building, designed to resemble a throne
• Explore Quincy ‘L’ station, preserved to look as it did when it opened in 1897
• See Alexander Calder’s vibrant red Flamingo sculpture in contrast with Mies van der Rohe’s stark Federal Plaza buildings
• Discover the neo-Gothic Fisher Building with its terracotta facade depicting fish, crabs, and mythical creatures
• Admire Chicago’s skyline from Grant Park, including distinctive structures like the Smurfit-Stone and Aon buildings

Take your time to enjoy this journey through one of America’s most architecturally significant cities, where each building tells a chapter of Chicago’s remarkable story.