Chicago grew from a prairie town to one of the world’s largest cities in less than 100 years. In the course of its growth architects pioneered the skyscraper starting in the 1880’s with the use of steel and large plate glass windows. Architectural design in Chicago conjures up the names of giants like Daniel Burnham, Charles Atwood, Louis Sullivan, Mies van der Rohe, and Stanley Tigerman. There are many varied styles and schools of architecture in the City of Chicago and you can see them all in a fun afternoon or evening on one of Chicago’s many architectural boat tours.

Here are a few favorites:

Chicago Architecture Foundation Center River Cruise: This 90-minute tour is led by knowledgeable docent volunteers who describe how Chicago became one of the most important architectural centers in the world. Selected as the #1 Boat Tour in North America by the USA Today Readers Choice Awards in 2021. The cost is $51.96 for the daytime tour and $55.74 for the evening. The boat can be accessed at 112 E Wacker Dr. For more information, go to

Skyline Lake Tour: Cruise the Chicago skyline on Lake Michigan on this 40-minute cruise and hear the history of Chicago’s buildings and how the famous skyline developed. Depart from Navy Pier at 600 Grand Ave. The cost is $26-$29 for adults and $10-$12 for children. For more information go to

Chicago Skyline Sail: View the Chicago Skyline from the S/V Windy, a traditional tall ship. The cruises are 75 minutes and you have three to choose from. At 1 pm you can learn about true stories of piracy, mayhem and mischief on the Great Lakes in the “Pirates and Maritime Stories Tour.” At 3 and 5 pm are the Architecture and Skyline sail. See the breathtaking views of Chicago’s skyline from out on Lake Michigan and hear stories of Chicago’s famous and iconic buildings. Finally, is the Sunset and Skyline Sail at 7 pm. The fee for adults starts at $39 and children $29. Set sail from Navy Pier at 600 E Grand Ave. For more information go to