As a gastronomic destination, Chicago is known variously as the land of deep-dish pizza, topping-laden hot dogs, and serious molecular gastronomy. But dive deeper into the city and you’ll find a vibrant, multifaceted culinary culture in the form of countless late-night taquerias, fragrant elote carts, and roaming tamale trucks. Boasting one of the largest Mexican communities in the United States (second only to Los Angeles), Chicago offers authentic, soul-satisfying Mexican fare without the pricey international airfare. Should you find yourself in town, skip the hot dog carts in favor of tastes of Oaxaca, Jalisco, Sonora, Veracruz — as well as local interpretations of classics that are uniquely Chicagoan. Here, our itinerary for a straight 24-hour shot of Mexican food, noon to noon.
Noon: Camino a Mexico
Begin your adventure south of the Loop in the predominantly Mexican neighborhood of Pilsen for a stroll through the National Museum of Mexican Art followed by a bite at Nuevo Leon Restaurant (1515 W. 18th St.; 312/421-1517). The restaurant is one of 20 Chicago spots honored with the Sabores Autenticos de Mexico award for authentic cuisine by the Consulate General of Mexico, so you know it’s the real deal. Opt for the chef’s special: a spicy stew of ribeye steak, tomatoes, jalapenos, and onions.
2 PM: Fun con queso
Hop on the Ashland bus and head north to La Lagartija Taqueria (132 S. Ashland Ave; 312/733-7772) to pick up an order (or two) of queso fundido. It’s one of the few places in the city you’ll find some variety within this common cazuelita (casserole): they offer five different kinds, including a spicy poblano chile and corn, and a version with pork al pastor, mushrooms, and poblano chile.
3 PM: Tamales del futuro
Melding a love for Mexican wrestling Sci-Fi films and tasty street food, Tamalli Space Charros is one of Chicago’s first food trucks, slinging both multi-media art and cheap tamales served by charros (Mexican cowboys) wearing lucha libre masks. If intrigue alone isn’t reason enough to track down the truck, the excellent flank steak with black mole or chicken with green-peanut mole should be.
5 PM: Rejuvenecer con guacamole
After running around all day, you’ll undoubtedly be in need of a snack to keep going on your taco adventure. Take a seat, rest your weary legs, and order up some fresh guacamole at Adobo Grill (1610 N. Wells St.; 312/266-7999), prepared tableside to the exact level of spiciness you can handle.
6 PM: Margaritas y platillos pequenos
Somewhere along the way, margaritas turned from a simple, elegant cocktail into a monstrosity of bottom shelf liquor cut with overly sweetened mixes served in gigantic glasses. Head to Rick Bayless’s justly famous Frontera Grill (445 N. Clark St.; 312/661-1434) for a taste of the real thing: a shaken margarita made seasonal ingredients and top shelf tequila from Cazadores Blanco or mezcal from Del Maguey.
8 PM: Rick Bayless, One plate at a time
Now that you’ve killed some time next door at Frontera during the inevitable wait for your table at Topolobampo (445 N. Clark St.; 312/661-1434), indulge in nuanced, unexpected flavors courtesy of Bayless’s high-end — but still faithful — adaptations of regional Mexican cuisine. He’s particularly known for his prowess with chili peppers and moles, and makes regular trips to remote parts of Mexico to foster his culinary knowledge and technique that he incorporates into a seasonally changing menu.
10 PM: Tamales y cerveza
Stake out a spot at the exceptionally popular Map Room (1949 N. Hoyne Ave.; 773/252-7636) in hopes of a chance encounter with the elusive tamale vendor Claudio Velez, a.k.a. The Tamale Guy. Known for his handmade tamales, Velez hops around West Side bars (trackable by the fan-operated Twitter account @tamaletracker) selling five-dollar packs of tamales to inebriated patrons. Even if he doesn’t stop by Map Room that night, you’re still sitting in front of one of the largest selections of craft and imported ales in town, including Mexican specialties like Pacifico Clara.
Midnight: Tacos y mas cerveza
As far as authenticity goes, the plaid-claid staff and patrons at Big Star (1531 N. Damen Ave.; 773/680-7740) skew more honky tonk than true taqueria. But none of the hipster posturing matters once you saddle up with a selection tacos like the al pastor, made with marinated, spit-roasted pork shoulder, grilled pineapple, onion, and cilantro. Beer, tequila, and whiskey are plentiful, with refreshing staples like Tecate and Modelo Especial to help wash down spicy dishes.
2 AM: Serenata del taco
As the rest of the city begins to shut down around 2AM, it’s prime time to head over to Lazo’s Tacos (2009 N. Western Ave.; 773/486-3303 ) for live entertainment and cheap drinks that keeps going well beyond most other places’ last call. The tacos aren’t quite as good as the tejano lounge singers, so head next door to Arturo’s (2001 N. Western Ave.; 773/772-4944) after a clumsy slow dance for some horchata and carne asada.
4 AM : Barbacoa bender
After having spent the past few hours stumbling through the busy streets of Wicker Park, head east towards the Ashland strip to La Pasadita (1132 N. Ashland Ave.; 773/384-6537) for late-night barbacoa. When you arrive, don’t be confused by the three separate buildings all claiming to be La Pasadita — they’re all owned by the same family. Rest assured, at least one of them will be open and serving tacos.
6AM: Carnita sunrise
Since you’re up anyway, it’s best to show up bright and early when Don Pedro Carnitas (1113 W. 18th St.; 312/829-4757) opens at 6AM on weekdays or 5AM on weekends; show up late, and you may have to fight your way to obtain an order of freshly made carnitas. In addition to hot and juicy meat, this is the ultimate adventure for open-minded epicureans interested in checking out chicharrones and offal tacos — eyes, tongue, brains. Make sure to stop by an ATM first, as this place is cash only.
9:30 AM: Desayuno
Complete the Rick Bayless trifecta you began the night before with a stop at Xoco (449 N. Clark St.; 312/334-3688) for breakfast: fresh churros and a selection of artisanal, bean-to-cup Mexican hot chocolates. (Try the Aztec, with a kick of chile and allspice.)
11 AM: Tortilla tour
Walk off breakfast with a tour through the Little Village neighborhood located on 26th Street between Western and Kostner. Stroll past street vendors selling elotes, tamales, Mexican hot dogs, and pozole. Make sure to stop off at Taqueria El Milagro (3050 W. 26th St.; 773/579-6120) for warm tortillas fresh off the press from the factory located next door.
Noon: Mexican Smorgasbord
End your journey with a mid-day feast featuring a little bit of everything. The nuevo-latino restaurant Mercadito (108 W. Kinzie St.; 312/329-9555) features a exhaustive number of guacamoles, ceviches, salsas, tacos, tortas, and other dishes designed to mix, match, and share. The unconventional offerings are among the best: Michoacan-style braised pork tacos come topped with chile de arbol coleslaw, and toasted peanuts; duck confit tacos feature prune mole and pumpkin puree. Top it all off with one of three kinds of flan, or a creme anglaise-soaked Mexican bread with vanilla ice cream and cajeta sauce.
Where to stay: The Wit (201 N. State St.; 312/467-0200)
Chicago isn’t much for Mexican-themed hotels, but you can experience a comfortable siesta with spacious, modern accommodations in the heart of the city at the Wit, where you can unwind with mini duck tacos (inauthentic, yes, but delicious) at their gastropub, State & Lake. Head upstairs to the rooftop lounge to kick back with a bottle of Victoria Cerveceria and a prime view of the city.
Carly Fisher is the Chicago editor of The Feast/Eat, a food and dining website. By day, she spends the bulk of her time with keyboard in one hand and banh mi sandwich in other. By night, she’s usually checking out obscure Belgian ales at her local watering hole.