On the southern curve of Mexico on the Pacific, the mountains and microclimates of Oaxaca have nurtured a number of distinctive foods. Oaxaquenos have had some time to refine their culinary tradition: 2,000-year-old Monte Alban was one of the first Mesoamerican cities.
The Oaxacan tamale is rectangular and made of smoothly ground cornmeal wrapped in a dark green banana leaf, which imparts a distinctive herbaceousness and slight color to the masa. Taqueria la Oaxaquena (6113 W. Diversey and 3382 N. Milwaukee) offers two types of Oaxacan tamales: a vegetable blend and a chicken mole, both tasty, though the powerful sauce somewhat overwhelms the vegetables. Off their "secret menu" you can get another Oaxacan specialty: chapulines, or roasted grasshoppers. They're slightly spiced with red chile and lime and can be sprinkled over tamales, mole, or just about anything else, though if you ask me they're most notable for the bragging rights they confer.
At El Paraiso (6011 W. Roosevelt, Cicero) yerba santa, an evergreen aromatic, provides the Oaxacan tamales with a tang not unlike a combination of peppermint and root beer. The masa they use here is exceptionally fine, but for a truly life-altering Oaxacan tamale go to the Maxwell Street Market, on Canal at Roosevelt, where most Sundays Tamal Oaxaca serves up big, beautiful clouds of masa stuffed with moist chicken and painted with just a touch of salsa verde and crema--simply one of the most delicious foods ever.
Quesadillas and Tlayudas
Oaxaca is renowned for its cheese, and queso Oaxaca is the main ingredient in quesadillas, every child's favorite Mexican food; unmelted, it's a lot like Wisconsin string cheese. It's also often sprinkled upon tlayudas, giant Oaxacan tortillas. These large, flat masa patties are lightly griddled, then roasted until crisp. In Mexico these are served at tlayuderias; in Chicago you can get 'em at Picante Grill (1626 S. Halsted).
Oaxaca is known as the Land of the Seven Moles, which seems to sell the place short given the sauce's infinite variations. In Chicago, mole negro is the most commonly found of the seven; on the Day of the Dead this dark pepper-and-chocolate mole is placed on Oaxacan altars to lure deceased family members back to the party. At Fonda del Mar (3749 W. Fullerton) a mole negro special, served with lamb, performs a delicate balancing act between heat and sweet. This newish Chicago restaurant from veterans of Topolobampo and Mia Francesca also occasionally serves up puerco en manchamanteles--pork in "tablecloth stainer" mole, a fruit-based sauce with peppery pineapple notes that works especially well with the roasted meat.
Adobo Grill (1610 N. Wells and 2005 W. Division) offers enchiladas in mole verde and mole rojo. The former, which contains large quantities of fresh herbs such as yerba santa and epazote, covers four curled tortillas filled with squash and mushrooms; the red sauce is served with chicken enchiladas.
Rick Bayless of Topolobampo (445 N. Clark) makes an effort to offer a range of moles on a rotating basis. A recent special (the menu changes monthly) was lamb with mole coloradito, made with anchos, chocolate, and almonds. Deep red and almost ketchuplike, it overwhelmed the meat a little, but coloradito tamales with cremini were excellent. Chuck Pine of Chuck's Southern Comfort Cafe (5557 W. 79th, Burbank, but currently closed for renovations after a fire), who used to cook under Bayless, whips up a mole amarillo, the yellowish and relatively thin member of the mole family made with costeno or chilcostle chiles, and folds it into quesadillas with chicken and yerba santa.
Around these parts one of the least commonly found moles is chichilo, a reddish version made with avocado leaves and the ashes of burned chile seeds and tortillas. Now that Geno Bahena has closed Chilpancingo, finding this mole in Chicago isn't getting any easier, though it is available at Ixcapuzalco/La Bonita (2165 N. Western), run by Geno's brother Tomas.
Finally, there's mole poblano, considered by some to be the definitive Mexican mole. The chicken in mole rojo at Ostioneria Playa Azul (4005 N. Broadway) is substantial with the deep, dusky flavor of poblano chiles. And--showing that Oaxaca doesn't have a monopoly on mole--at May Street Cafe (1146 W. Cermak) chef-owner Guadalupe Aguilar makes a Michoacan mole with pasilla and ancho chiles and just a bit of chocolate, aiming, she says, for "less sweet and more heat."