Italian beef sandwich at Al's Beef on Taylor Street (Kate Bernot )
Lately, the crowds strolling Little Italy's main drag, Taylor Street, are just as likely to be in search of a craft cocktail as clams casino. In the past few years, the street has welcomed fresh faces such as lively restaurant and wine bar Davanti Enoteca, punk gastropub Three Aces and charming small-plates spot Urban Union. But if you've experienced only the new kids on the block, it's time for a history lesson: Many of the area's culinary legends have existed for decades and helped establish the neighborhood as an Italian mecca. This half-mile stretch of Taylor Street provides a crash course.
FIRST: Al's Beef, 1079 W. Taylor St. 312-226-4017
In 1938, Al Ferreri and two of his family members introduced the city to the now-iconic Italian beef sandwich: thinly sliced, marinated beef, peppers and spicy giardiniera on a soak-it-all-up roll ($5.50 for a regular; $7.70 for a large). The original location is steeped as much in history as it is in juicy gravy, so you'll get a taste of old Chicago as you lean over the counter in the perfect sandwich-eating "Italian Stance."
THEN: Mario's Italian Lemonade, 1066 W. Taylor St.
Whatever you do, just don't call it "Italian ice." Mario's serves Italian lemonade, and the plain lemon flavor ($1.50 for a small; $2.50 for a medium) at this red-, white-, and green-painted stand is simple, but leagues better than competitors. It's a little sweet, a lot tart, and flecked with actual pieces of lemon peel. The only time to choose another flavor would be when Mario's happens to be serving its elusive, seasonal peach flavor. Order from the front window, then try to avoid a brain freeze as you wander west on Taylor. Since 1954, Mario's has been synonymous with summer, and it's open May through September.
LAST: Conte di Savoia, 1438 W. Taylor St. 312-666-3471
Finish your excursion the way a true Italian would, with an espresso. Market and deli Conte di Savoia is known for its piled-high sandwiches, but caffeine freaks know the Illy espresso ($1.42) served here is as good as what you'd get across the Atlantic, and the 10-ounce cappuccino for $1.50 might be the best deal in town. You probably won't be able to stomach any more goodies after this meal, but peruse the shelves for imported meats, cheeses, pastas and oils to take home as souvenirs of your excursion.
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