The history of the Bridgeport and Armour Square area is as old as Chicago itself. Native Americans used the area as a portage, particularly when the Chicago River was at its deepest, and most spread out. Later, Father Jacques Marquette and Louis Jolliet explored the region in 1673, proposing the addition of a canal to aid in the region’s natural use as a transportation center and trading route. Some 175 years later, the Illinois and Michigan Canal created jobs and enabled industries and fueled the growth of the Bridgeport area and the city of Chicago. Freight and passenger rail followed by commuter rail expansion divided the areas of Armour Square and Bridgeport, and fenced in the areas by hard boundaries like the South Branch of the Chicago River and the rail lines. The expansion of the Federal Highway System and the construction of the Dan Ryan and Adlai E. Stevenson Expressways and various merging ramps and exits further served to cut off the two areas from one-another, and in many ways, the areas from the rest of the city, despite its past as a transportation hub.

The built history of the region is fascinating in both its plethora of early examples of architecture that still survives, and a long history of styles, marking the expansion of different immigrant communities into the area, and the changing of architectural norms. There are more than 200 notable buildings and locations along the way of the ride, with over a dozen stops and detailed explanations of the buildings, their history, the background of the area, and the story of two of Chicago’s most fascinating communities.