If the last time you visited Pilsen was for brunch at Nightwood or a hangover-curing bowl of menudo at Nuevo Leon, it's time to return. This lineup starts on 18th Street and covers a bit more than a mile of ground on the way over to Halsted; hop the #18 bus if you're not up for the leisurely stroll along the neighborhood's main drag.
FIRST: Nitecap Coffee Bar (1738 W. 18th St. 312-846-1149)
Take the Pink Line to fuel up for the day at this month-old cafe just a few steps west of the 18th Street station. The owners brew local roaster Metropolis and make their own caramel and chocolate syrups to flavor its lattes ($3.20-$4.20). The bakery case temps with treats such as cupcakes, muffins and cookies (some vegan), including made-from-scratch kolaczki, a traditional Polish cookie
NEXT: Dia de los Tamales (939 W. 18th St. 312-496-3057)
Work up an appetite for lunch by walking east along 18th Street and browsing vintage and resale shops on your way to this recently opened tamale shop with a façade decorated with Day of the Dead-style skulls on the façade. It's kind of like a Hot Doug's for tamales ($3 apiece), with rotating specials and funky fillings ranging from slow-roasted pork with ghost pepper-spiced Apocalypse sauce to coconut-curry chicken to Italian beef and giardiniera. The vegan tamale made with spicy black beans and corn sold out on opening day two weekends ago. The current set-up is grab-and-go, so nosh on your tamales as you continue down 18th Street toward Halsted.
LAST: Chocolat Uzma Sharif (1823 S. Halsted St. 312-694-3471)
End your excursion on a sweet note at this artisanal candy shop, holding court amongst art galleries since last June. Inside, picture-perfect creations from owner and chocolate maker Uzma Sharif--a former pastry chef at Puck's Cafe inside the Museum of Contemporary Art--range from chili-spiced caramels to chocolate discs sprinkled with candied rose petals to a toasted coconut and lime chocolate bar. Select your favorites from the chocolate bar (99 cents to $2.25 per piece) or ask Sharif to pack up a multi-piece box with your selections (or hers). Take your treats to-go or linger with a cup of Rishi tea or dark Belgian sipping chocolate ($2.79).
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