What better place to start than on a Chicago Architecture Foundation tour? With 85, walking, bus, and boat tours available, you have plenty of choices. You definitely don't want to miss their popular summer River Cruise boat tour aboard Chicago's First Lady - the official boat tour company for the Chicago Architecture Foundation.
Don't miss an architecture boat cruise with Chicago Line Cruises, Shoreline Sightseeing, and Wendella Sightseeing Boats. All offer great views and great stories of Chicago's iconic skyscrapers.
Of course, your feet can show you the sights as well. In addition to its Signature Architectural + Historical Walking Tour, Chicago Savvy Tours guides you through the works of specific architects, the city's vast system of underground roads and tunnels, and other fascinating sites. Then there is the Chicago's Finest River Walk Tour, which highlights -- you guessed it -- the Chicago River and its icons. Finally, if you want to explore on your own terms, try Metrowalkz Self-Guided Walking Tours. For less than $12, you can download all sorts of audio tours including one on Loop Architecture.
No other architect has had quite the mark on the Chicago area as Frank Lloyd Wright. The Frank Lloyd Wright Preservation Trust offers tours of the Rookery Building in downtown, the Robie House in Chicago's Hyde Park, and FLW's home and studio in the nearby suburb of Oak Park. Additionally, the Unity Temple in Oak Park is one of Wright's seminal works and definitely worth the trip. You can easily access Oak Park via the CTA "L" train. Really, you have no excuse not to go!
Please note: Some of the above tours are available seasonally and are weather dependent. Please check with each tour company for availability.