Things To Do In Old Town

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.

Comedy Is King

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:

  • The J. Parker: Sitting atop Hotel Lincoln, this rooftop drinking and dining spot 13 floors above Clark Street offers spectacular views of Lincoln Park and Lake Michigan beyond North Street Beach.
  • Kamehachi: Was Kamehachi Chicago’s first sushi restaurant? Maybe, maybe not. But opening in 1967 across from The Second City, it’s certainly the place many Chicagoans — and visiting celebrities — first experienced this Japanese favorite. Like its neighboring comedy troupe, Kamehachi (meaning “eight turtles”) is still going strong.
  • The Old Town Ale House: Billing itself as the premiere dive bar in the world and featuring its vulgarian/political satirist/blogger/co-owner, the 60-year-old ale house harkens to Old Town’s bohemian roots. The jukebox is heavy on jazz and blues — a plus according to Bruce Elliott, the above-mentioned co-owner, because, “Punks hate the music and don’t come in often.”

There’s Always More

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.