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Cruising the Chicago River

Posted on June 1, 2025August 31, 2025 by Stephen Edwards

Chicago is a town that inspires when it comes to its architecture, and the best way to appreciate an overview of what the city has to offer is via a cruise on its namesake river.

Chicago during a late July Sunset, a great time to enjoy the city!

The Chicago River is an engineering marvel as it originally flowed into Lake Michigan. The river’s course officially reversed in 1900, with the completion of the canal emptying in the Mississippi River watershed. Because of the canal locks, boats can now navigate between the Great Lakes and the Mississippi River. The reversal of the river through the canal locks has also created an iconic American journey, the Great Loop.

Adrienne with Navy Pier in the background. This part of the river was one time the mouth, but now it is where Lake Michigan will empty back into the river.

We opted for a sunset Chicago Architecture Tour to see the buildings along the route during the golden hour. Chicago has fully embraced its watershed, and the buildings along the banks of the river incorporate watersheds into their design. It was a relaxing cruise on a summer afternoon, and our guide was excellent at sharing stories about the buildings we passed.

The sunset cruise quickly turns into an evening cruise. Chicago’s iconic skyline also provides for great views during the evening.

Chicago provides a great example of how cities can incorporate water into the city, and taking a couple of hours to float on the river is a great way to appreciate the city.

To book a cruise, several companies offer bookings. We booked through Wendella Tours and Cruises and I strongly recommend them for a great experience.

The Willis Tower (Spelled S-E-A-R-S in Chicago) as seen from the river at night. At one time, this building was the tallest skyscraper in the world from 1974-1998.

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