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Old Town Chicago

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…a hip re-creation of hippie roots
 
Part of why Old Town is so cool is that it used to be a center for artists and progressives in Chicago.

Just north of downtown, between the sparkling Gold Coast and pristine Lincoln Park, Old Town is now a mix of old and new (mostly new)—a bit historical, a bit trendy—with entertainment and nightlife options in casual, chic or high-glam. It varies a lot from street to street, making it one of the most interesting and relatively safe neighborhoods to wander.

The Old Town Triangle, with its narrow, brick-paved streets, cute cottages and row homes, contrasts starkly with Division Street, which late in the week, writhes with frat boys and their female counterparts who attempt to stay standing ‘till dawn. A few blocks away, Wells Street and North Avenue hop with bars, comedy clubs and Pipers’ Alley, which has a movie theater and the famous Second City spaces. After a show, it’s a quick walk to The Old Town Ale House, a relic that still serves strong cocktails among interesting people.

Old Town is a lot different from the hippie haven it was in the 60s, but you’ll still see the occasional throwback to its raw, historical past—like a commemorative plaque on the side of a new, luxury high-rise condo building.

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Known for:

The Second City

Main drag:

North Wells Street

Old Town Chicago blogs and events

Catch a Rising Star at Donny’s Skybox

Donny’s Skybox is tucked away on the top floor of the Piper’s Alley Complex at 1608 North Wells Street in the Old Town neighborhood of Chicago. The charming, little cozy theater really makes audience members feel like they are part of the performance.

Earlier posts >

Apartments in Old Town Chicago