Tours and Excursions: What better way to learn about a city than on a tour? Chicago Trolley Company offers an informative, entertaining method of experiencing Windy City history. Twelve stops are included, and sites feature everything from the origins of the Great Chicago Fire to current architectural wonders. Since trolleys pick up and drop off every 30 minutes or so, you can purchase an all-day pass and come and go as you please. The entire 13-mile loop takes two hours if you go straight through.