Chicago’s location at the crossroads of water, rail, and later air transportation has always made it a place of exchange: in the late 19th century, it funneled the wealth of an agricultural hinterland the size of Western Europe through its grain elevators, riverfront piers, and—ultimately—its financial institutions. In the 20th, infrastructural and residential construction nourished its better known downtown skyscrapers with flows of labor and wealth to reshape and rebuild the city. Looking at the arc of Chicago’s building history reveals changing politics and economics that allow us to see a broader narrative of construction—as both an end result and a lever of political and financial power.