Chicago is a transportation center, and it once was home to a thriving port:

In 1871, the city’s one-of-a-kind water link between the Great Lakes and the Mississippi River helped make it the country’s busiest port, one that lured more ships than New York, San Francisco, Philadelphia, Baltimore, Charleston and Mobile combined, according to the Encyclopedia of Chicago…

These days, Chicago is much better known for busy railroad lines, air traffic, and highways.

Intriguingly, Chicago still has access to major bodies of water. Whether they are in as much demand as the past and whether they are in good enough shape to handle more traffic (the subject of the article cited above) are other matters. Could there be a future world where more goods and materials go by ship and Chicago benefits from its location that can link the Atlantic, the Great Lakes, and the Mississippi?