It’s official—Chicago is home to one of the coolest streets in the world (again!).

Roscoe Street is No. 28 on Time Out’s annual rankings of the coolest streets in the world . Barely a mile west of Wrigley Field lies “the village within the city”: Roscoe Village , a quaint, family-oriented neighborhood lined with three-story walk-ups, local watering holes and quirky boutiques. There’s an almost cinematic friendliness to Roscoe Street, the Village’s main thoroughfare: parents swapping weekend plans while kids pop wheelies on the sidewalk, bartenders regaling patrons with vivid stories and free shots, bakeries remembering regulars’ orders by heart.

In the summer, you’ll find Chicagoans flocking to Roscoe Street to celebrate Retro on Roscoe , an annual festival where antique vendors an

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