The Cherry Avenue Bridge is an asymmetric bob-tail swing bridge in Chicago, Illinois that carries the Chicago Terminal Railroad, pedestrians, and cyclists across the North Branch Canal of the Chicago River. It was constructed in 1901–02 by the Chicago, Milwaukee and St. Paul Railway, and it is a rare example of this type of bridge; it was designated a Chicago Landmark on December 12, 2007.

The Chicago River is a system of rivers and canals with a combined length of 156 miles (251 km) that runs through the city of Chicago, including its center. Though not especially long, the river is notable because it is one of the reasons for Chicago's geographic importance: the related Chicago Portage is a link between the Great Lakes and the Mississippi River Basin, and ultimately the Gulf of Mexico.