Old Town

Upscale 19th century townhomes and cobblestone streets characterize this picturesque neighborhood on the city’s Near North Side. Visitors are drawn to Old Town by its vibrant dining scene, plentiful boutique shopping and thriving entertainment district that includes several world famous Chicago theater institutions, including the Second City improvisational comedy club, the Steppenwolf Theatre and Royal George Theatre. Old Town is also home to one of the nation’s oldest annual summer art fairs.

Old Town: One of Chicago’s Great Destination Neighborhoods

Written by Alan Solomon, with research assistance from the Chicago Neighborhood Tourism Project.

Old Town is -- and always has been -- one of Chicago's great destination-neighborhoods. It's that simple.

Yet locals -- and especially locals older than, say, 50 -- find it irresistible to regale visitors with tales of what it was, not because it was necessarily better back then but because Old Town for a time seemed to reinvent itself every 10 or 15 years, and that makes for individualized sets of memories.

There was the artist era when rents were cheap, then the folkies took over Wells Street and then the hippies and then the gentrifiers. For a time, Ripley's Believe It or Not provided a certain . . . presence. There were burger places and bars with peanut shells on the floor, and across the street an adult club next to a French restaurant and down the street a steak joint next to Second City, which was across from Earl Pionke's pub. (How sweet the sounds that flowed with the beer at The Earl of Old Town.)

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