Local Secrets: An Insider’s Guide to a Weekend in Chicago

Apologies to Ferris Bueller, but there’s more to do on a day off in Chicago than catching a Cubs game at Wrigley or visiting the Chicago Art Institute.

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Apologies to Ferris Bueller, but there’s more to do on a day off in Chicago than catching a Cubs game at Wrigley or visiting the Chicago Art Institute. Those are certainly worthy attractions, but taking a deeper dive into the Windy City reveals a whole host of options that allow you to experience Chicago like a native. From taking in a blues show to indulging in an Italian beef sandwich, take time to scope out the local best.

Blues Alley

black and white close up shot of man's hands on the neck of a guitar while playing blues on a jazz guitar at a venue in Chicago, IL

If you want to bring a crowd of Chicagoans to their feet singing in unison, play the song nearest and dearest to their hearts: “Sweet Home Chicago.” You might hear the blues classic on a visit to one of the city’s many blues clubs, such as Buddy Guy’s Legends or Blue Chicago downtown, but ask a local where to go, and you’re likely to hear about Blues Alley on Halsted Street in Lincoln Park.

The top club in the area is Kingston Mines, a city institution since 1968 that features the gritty Chicago blues sound 365 days a year. Blues luminaries from Koko Taylor to Magic Slim have graced the stage in this rockin’ club that plays music well into the wee hours. (The last set starts at 3:30 a.m. on Saturdays.)

Italian Beef

A close up view of a hearty Italian beef sandwich with French fries, served in a restaurant in Chicago, IL

Famous Chicago dogs and deep-dish pizza are readily available on every layover at O’Hare, but another local culinary dish is overshadowed far too often by these more famous bites. Originating in the city in the 1930s, the Italian beef sandwich is made of thin slices of seasoned, melt-in-your-mouth roast beef, simmered and served with au jus gravy on a long Italian roll. Don’t forget the peppers, hot or sweet. Every neighborhood has an Italian beef joint — maybe more than one — but Johnnie’s Beef in Elmwood Park, Al’s #1 Italian Beef on Taylor Street, and Portillo’s are the clear winners if you want a true Chicago culinary experience.

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Bucktown Shopping

The city’s many neighborhoods bring a flavor all their own to the stew that is Chicago. Just northwest of downtown along the Chicago River, the neighborhood of Bucktown is an absolute shopper’s haven. Shops and boutiques line Damen Avenue, fully stocked with some of the hottest clothing and accessories this side of Paris. Check out the hyper cool RSVP Gallery, a below-ground shop that mixes streetwear with art and high fashion, or p.45 featuring both local and international designers.

Black Box Theater

Where do you think many of the great Chicago playwrights and actors got their start? The city’s black box theaters — simple, unadorned performance spaces — put on great shows even before actors Gary Sinise and Terry Kinney started Steppenwolf Theatre in 1974.

Check out a play at one of many venues around the city, including Writers Theatre, House Theatre of Chicago, or The Neo-Futurists, to enjoy everything from original productions to adaptations for novels like “1984” and Alfred Hitchcock’s “The 39 Steps.” For something more tried and true, the acclaimed Chicago Shakespeare Theater at Navy Pier produces Shakespeare plays and other shows with impeccably high production values.

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