Artsy, funky, funny and friendly, Old Town might be the most eccentric among Chicago’s affluent enclaves. A perfect location nestled in the near North Side sweet spot between Navy Pier and Lincoln Park, it largely eschews high-rise living for narrow, tree-lined streets with the beckoning stoops of stately Victorians.
Yet, while long on charm, many Old Town attractions make the neighborhood equally long on charisma.
Where to visit first? Unquestionably, Old Town is most famous for The Second City — ground zero for improv comedy. It began as a small cabaret theater in 1959 and soon grew into an influential movement that changed the way comedy was created and consumed.
Joan Rivers, John Belushi, Bill Murray, Tina Fey, Amy Poehler, Steve Carrell and Stephen Colbert — along with dozens of other comedy superstars — have all graced The Second City stage.
Beyond The Second City, Old Town attractions in the comedy milieu include The iO Theater, which relocated from its Wrigleyville roots as the ImprovOlympic to a large, four-stage spot on Kingsbury Street in 2014; and Zanies, which upon its opening in 1978 became the city’s first venue offering stand-up comedy on a full-time basis and now claims to be the only comedy club in the country featuring nationally touring headliners nightly.
There many more things to do in Old Town that will put a smile on your face. For instance:
A Red Orchid Theater, co-founded in 1992 by Oscar-nominated actor Michael Shannon (the Shape of Water, Nocturnal Animals), is “dedicated to the proliferation of live theater in the modern world.” The Fudge Pot (creating handmade confections since 1963) is where to visit if satisfying your sweet tooth is the priority. Old Town Pour House has more than 90 craft beers on tap.