Chicago’s richly textured and infinitely walkable neighborhoods deliver the quintessential urban experience without the big-city price tag. Whether you hit the pavement in leafy Lincoln Park, gritty Pilsen, or hipster enclaves like West Town and Logan Square, you’ll discover cheap eats, free museums, and—when the cold winds aren’t blowing—an almost overwhelming number of outdoor events where the fun is free of charge.
National Museum of Mexican Art
It’s only fitting that Chicago—home to the second-largest Mexican population in the United States—would have a world-class museum dedicated to Latino arts. Located just west of the bustling 18th Street corridor in the colorful Pilsen neighborhood, the museum represents a crash course on the story of the Mexican experience: from indigenous Mayan and Aztec cultures through the colonial period, the Mexican revolution, and 20th-century equality movements. Entry is free all year long.
Fine dining is broken down to the barest essentials at this 32-seat steampunk bistro on Ashland Avenue in West Town. The menu of Asian-tinged, eclectic American dishes changes seasonally, but staples include a daily crudo selection and maple-soy-glazed black cod. Somehow, the dining room’s vintage and repurposed aesthetic—making excellent use of old theater seats, church pews, and other design castoffs—radiates warmth, not pretentiousness.
Reno, Logan Square
The views of Logan Square’s historic, tree-lined boulevards make the pumpkin seed bagels at this rustic breakfast-lunch-dinner spot taste all the more perfect. Come back in the evening, when the wood-fired ovens crank out pizzas with creative toppings like savory-spicy pork belly carnitas.
Logan Square’s residents cheered the reopening of this 1915-built movie house, which has been refurbished in all of its Art Deco glory. Film showings range from new releases to indies and cult classics. Don’t forget to pop into the retro-tinged bar lounge for a post-flick pour from nearby craft brewery Revolution Brewing.
Dusty Groove America
Those on the hunt for soul classics—as well as classic and contemporary jazz, funk, and reggae beats—can easily kill a day digging in this renowned record shop’s bins overflowing with CDs, LPs, 45s, and other music of the nondigital and downloadable variety.
A stellar bourbon list and a thoughtful craft beer selection make this vintage tin-ceilinged tavern worth the trip off the beaten path. Dim lighting and cool jazz set a chilled-out, retro mood. The closest thing to sports action is the free shuffleboard game in the back.
While wandering down Milwaukee Avenue, be sure to stop at the indie-minded startup Shop 1021, which sells a selection of well-edited gifts such as Fred glassware.