The Chicago Architecture Foundation’s Chicago River Cruise is great.  Several companies offer tours, but the CAF tour is generally recognized as the best one to take because of the knowledge of the docents from the CAF.

The docents on the boat during the hour and a half tour point out many architectural highlights in Chicago that can be viewed from the river, including The Fulton House, The Merchandise Mart, Lake Point Tower, Sears (AKA Willis, lol) Tower, and others.

They also discuss the various styles of buildings and the progress as materials and styles changed over the decades.

The docents do this for the love of the city, and have to earn a lot of facts to be approved to do the tours.  There is competition to get to do the tours.  They also don’t take tips.  This is just something they love to do, and it shows.

If you’ve done one (or can’t do one) and want to get an idea of what you’d learn, the CAF has made a book with way more info than they could ever do in a tour and with pictures of many buildings. Click on the picture of the book for more info.

They discuss the history of Chicago, starting around Fort Dearborn and then continuing through the Chicago Fire and the reversing of the river (to lead downstream, rather than into Lake Michigan).

Bring sunscreen and other protective gear if you are sensitive to the sun.

You can get a book of the experience from the people who do the tour: