Chicago Guide

Can’t-Miss Chicago Architecture Experiences

Explore the cityscape that transformed architecture forever.

Chicago is home to some of America’s favorite moments in history: pizza, jazz, and (for some) the Chicago Cubs. Yet, our big-shouldered city’s true claim to fame is something much taller. In fact, it was the world’s first skyscraper built right here that put Chicago on the map – literally and figuratively. To truly discover what our hometown is all about, you need to explore the steel-and-glass icons that changed the game for architecture everywhere. 

Below, check out a few unique experiences not-to-be-missed during your next visit to the birthplace of modern architecture. 

Wright Around Chicago

WHERE: Wright’s sites (of which there are many)

WHY?: On this expert-led bus tour, enter the mind of perhaps the most famous American architect, Frank Lloyd Wright, and others who shaped the city with their work. Explore Chicago while traveling around the city to visit iconic landmarks that impacted architectural history. The Rookery Light Court downtown and Wright’s home and studio in the charming Oak Park neighborhood are just a few of the spectacular feasts for the eye.  

Chicago for Chicagoans Tours

WHERE: Chicago neighborhoods 

WHY?: One of the best ways to experience the architectural culture of this city is by “living like a local.” During this tour, Chicagoans and travelers alike are invited to walk the streets of different Chicago neighborhoods while residents share community history and the stories behind them.

Elevated Architecture

Downtown “L” Train

WHERE: The Loop 

WHY?: This tour takes places more than 20-feet above the ground and at this level, you’ll see parts of Chicago you’ve never seen before. Go for a 2-hour ride in the city’s first elevated train as it travels deep through the Loop and all its history. There, you’ll discover how the “L” system became a defining moment in Chicago architecture and the heartbeat of the city today.

Pro Tip: If you can’t get enough of Chicago’s Greystones, but don’t have time to tour them all on one visit, here’s a quick plug for you. Every October, the Chicago Architecture Center hosts Open House Chicago, a festival featuring more than 270 Chicago buildings opening their doors for self-guided architecture tours to the public. 

Chicago Architecture Biennial

WHERE: Michigan Avenue 

WHY?: During this exhibition, get an up-close look at modern issues within architecture and explore the innovative solutions behind them. With the Biennial as our neighbor at the Chicago Cultural Center, stop by two of Chicago’s oldest skyscrapers along the way – the Wrigley Building and Tribune Tower. 


WHERE: Well, right here under our storied roof.

WHY?: End the day right where you started by learning all about the history and architectural details and gems that were preserved and restored in our Venetian Gothic landmark building, designed by Henry Ives Cobb. The Chicago Architecture Center walks you through all the old world craftsmanship restored to its original elegance, plus renovated and newly added spaces.

Find your home base here and get ready to explore all the best architectural gems.