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This weekend, more than 50,000 runners will line up for the Chicago Marathon—and Bandit Running will be there to capitalize with a pop-up inside Tribune Tower. Next month, the Brooklyn-based brand will open its first brick-and-mortar outpost in the city, located just off a popular running trail in the Bucktown neighborhood. It’s a calculated expansion: Chicago has become Bandit’s second-largest e-commerce market, behind only New York City, where co-founder and C.E.O. Nick West told me the brand has capitalized on an “amazing subculture” of running.