The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady Cruises, which calls upon expert docents provided by the Chicago Architecture Foundation to reveal extensive history, culture, and style insights (for example, how the design of Willis Tower was based on cigarettes, or how the Monadnock Building on Jackson Boulevard was fabricated with 100 different shapes of brick). Book anytime between May and November for these rides, which run every day of the week and last 90 minutes.
