I recently visited the Chicago Portage National Historic Site in Lyons, Illinois. Here are some images from the site:

The importance of traveling via water meant that portage sites were important. This site was one of the places where it was easier to move watercraft from the Great Lakes system to the Mississippi River system. It was not the only portage site allowing that connection but it became known and then improved on in the mid-1800s with a canal.

The site now is somewhat obscured off a major local road and close to a major interstate. The area is mostly industrial land with few houses nearby. Chicago is a transportation center but a portage is no longer needed. There are still canal waterways nearby but these have receded in importance to and status in Chicago compared to railroads, highways, and airports. Chicago is still a transportation center but a portage is no longer needed.

The Chicago Portage Wikipedia page has lots of details.