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A close-up shot of flowers in a tree-lined street in Old Town neighborhood
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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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CTA Public Transportation:

El: Brown Line to Sedgwick. Bus: 11, 22, 36, 72. For more travel information, visit www.transitchicago.com.

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Unless otherwise noted, each site on this map has identified itself as wheelchair accessible.

Old Town continued...

 

And on North Avenue journalists (Ebert, Royko, others) would drink beneath giant images of Behan and Shaw, joined late by Second City unknowns until closing time at that 2 o'clock bar forced them to the 4 o'clock bar, the one with Billie Holiday on the jukebox . . .

See?

Here's what Old Town is today: It's Wells Street, mainly, with its restaurants -- some of them among Chicago's best -- and places that make you laugh and some that make you think, just enough bars, plus shops. It's the Old Town Art Fair and its semi-sibling, the Wells Street Art Fair, every June. Among the fancy boutiques and the galleries, along with the fudge shop and the cigar store (complete with Indian), there's a supermarket and a drugstore, a dry cleaner and a couple of places to buy flowers, a shop to buy fish food and another to get a bicycle fixed and a barber shop.

Taken together, they keep Old Town a living neighborhood, not a theme park. Enjoy its food and drink and entertainment, but walk a block or two along the side streets west of Wells and you'll discover why this place is Old Town.

Most of the original buildings burned to the ground in the 1871 Great Chicago Fire; St. Michael Church, built on Cleveland Avenue in 1869 of brick in what was a wooden city, was a partial survivor (and quickly restored). What you see on those side streets, along with the landmark church, are some of the brick Victorians and working-class cottages that literally rose from the ashes. Much of it is within the Old Town Triangle Historic District, which is on the National Register.

Sometimes the history isn't so obvious. The Second City, the legendary incubator of comedy talent on Wells just north of North, has its own history; its roots are in the Hyde Park neighborhood, but it moved to Old Town in 1959 and into its present building in 1967. Performers launched on its stages include Ed Asner, Alan Arkin, both Belushis, Gilda Radner, John Candy, Bill Murray, Chris Farley, Harold Ramis, Tina Fey and so many more -- and the revues keep coming, there and at its annex, Second City ETC.

That's the obvious history. For the subtle, look at the ornamental work that frames the entrance. It was salvaged from the Loop's Garrick Theater, an Adler-Sullivan masterwork flattened by wreckers in 1960.

Laughs also can be found most nights at Zanies, a Wells Street stand-up venue for more than 30 years. Across the street, A Red Orchid Theatre -- Oscar nominee Michael Shannon ("Revolutionary Road") is a founding member -- has been challenging audiences since 1993.

So many restaurants on Wells: Salpicón is cutting-edge Mexican. Orso's is neighborhood Italian; Kamehachi introduced the sushi bar to the neighborhood (and the city) in 1967; the Fireplace Inn is neighborhood ribs. Old Jerusalem is a longtime favorite for Middle Eastern fare. Topo Gigio, also Italian, is named after a puppet but is serious about its pastas and veals. Bistrot Margot, French; O'Brien's, steaks; Adobo Grill, its own signature Mexican. More . . .

The visitor's Old Town isn't just on Wells. Twin Anchors, a bar-restaurant whose ribs have been praised by Frank Sinatra, anchors Sedgwick Street as it has since 1932. Halsted Street, a few blocks west, is home to Steppenwolf Theater, whose Tony Award-winning ensemble includes Gary Sinise, John Malkovich, John Mahoney, Joan Allen, William L. Petersen, Tracy Letts, Laurie Metcalf and many other performers and writers. Across Halsted is the Royal George, whose productions have delighted audiences for years.

In Chicago, where there's theater, there are restaurants -- and the Halsted theater district has more than half a dozen, including Alinea, ranked by critics among the world’s elite.

But if all you want is a drink and some Billie Holiday, that's still here. The jukebox maybe digital now, but the Old Town Ale House, on North Avenue a block west of Wells, is still the Ale House. Just like St. Michael is still St. Michael.

Some institutions, even in Old Town, defy reinvention.

 


For more information, please contact the Old Town Merchants & Residents Association at 312.951.6106.

 
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