Grab a slice of tres leches cake and an horchata latte—made with rice water and locally roasted Intelligentsia espresso—at Kristoffer’s Café & Bakery. This unassuming coffee shop is known for its Mexican desserts. 1733 S. Halsted St.; 312-829-4150.
Take a (free) spin through the National Museum of Mexican Art to view a collection that includes Mesoamerican artifacts, contemporary prints, and paintings.
At Nuevo Léon, a mom-and-pop Mexican joint, try the rib-eye-and-onion-filled “tacos de sabinas,” named after a nearby tortilla factory. Tacos $5–$8.
Browse the many vintage stores on 18th Street, including the must-visit Revival a Go-Go, which sells a wide array of 1960s clothing and collectibles, from mod dresses to Midcentury Modern couches.
The 16th Street rail embankment—a 14-block stretch of vibrant murals—is a picturesque place for an afternoon stroll. Look for politically and culturally charged works by Gaia, ROA, and others.
Graze on eclectic small plates by Longman & Eagle alums, like choucroute with garlic sausage and pickled apples, at Dusek’s Board & Beer. Entrées $15–$32.
Historic Thalia Hall is fresh off an extensive face-lift; catch live music from indie acts like Edward Sharpe & the Magnetic Zeros.
The 1970s-inspired basement bar Punch House serves largeformat drinks in 40-ounce bowls. Order the Space Juice for Jered, made with tequila, grapefruit, sparkling wine, and sage.