Big Star What compelled a James Beard Award–winning chef and the owners of the city’s most exclusive cocktail lounge to open a divey bar that slings Tecates and whiskey shots for $3 apiece? A stroke of absolute genius. Brutal crowds harsh the country-music mellow on weekends, but neighborhood hipsters put up with it, dropping by the takeout window to grab a couple of tacos or planting themselves at the wall-length counter for a few beers or quality cocktails. 1531 N Damen Ave (773-235-4039). Sun–Fri 11:30am–2am; Sat 11:30am–3am. Average beer: $4.
Cafeteria Marianao Don’t go expecting tablecloths and doting waiters—this Cuban lunch counter is no-frills, and that’s just fine with the regulars who line up every morning for their eye-opening café cortado and a warm toasted sandwich. You’d think the Cubano sandwich is the required order, but the big draw is the steak: thin slices of juice-dripping beef piled onto fresh bread, topped with griddled onions and toasted on the hot press. It’s usually standing-room-only here, so grab some plantain chips and a soda and head for the parking lot if you want to wolf down your lunch in peace. 2246 N Milwaukee Ave (773-278-4533). Breakfast, lunch. Average main course: $5.
Doughnut Vault At this Brendan Sodikoff venture, doughnut makers using the noms de plume François and Henri Gras put out batches of vanilla glazed, chestnut, buttermilk old-fashioned and other doughnuts of both the cake and yeast varieties. And these are marvelous doughnuts—perhaps the best you will ever have. Naturally, there are long lines, and the Vault regularly runs out of wares by early afternoon. So wake up early, and check the official Twitter account (@doughnutvault) often. 401 N Franklin St (312-464-9544). Tue–Fri 8:30am–sold out, Sat 9:30am–sold out. Average doughnut: $3.
Gene & Jude’s Red Hot Stand Do not ask for ketchup when you order one of the legendary slender, snappy hot dogs that come topped with a fistful of fries at this SRO institution that’s been serving ’em up since 1951. The surly types behind the counter don’t go for sissy stuff like that. Claim your place at the end of the perpetually long line and entertain yourself by watching potatoes being cut and fried into perfect greasy strips while you wait. Once it’s your turn, order your dog with everything, then count your blessings for the wax paper–wrapped bliss that lies before you. 2720 N River Rd, River Grove (708-452-7634). Lunch, dinner. Single dog and fries: $2.50.
Lem’s BBQ As the best barbecue joints on the South Side do, Lem’s requires that you order through bulletproof glass and then eat your ribs standing in the tiny vestibule, or take them elsewhere (a.k.a. your car). But it would take much more than that to scare away devotees of these spareribs and rib tips, which have a thin, vinegary sauce heavy with spice and charred outer edges that hide pink, juicy pork. Honestly, the only truly scary thing here is arriving to find the line snaking out the door. 311 E 75th St (773-994-2428). Lunch, dinner (closed Tue). Average main course: $12.
Superdawg Drive-In Despite a renovation in 1999, this hot-dog drive-in is still as old-fashioned as ever, with uniformed servers bringing your order directly to your car window (that is, if you choose not to eat standing in the restaurant proper). Apparently scared of copycats, the owners have trademarked almost every dish, the main draw being the “Superdawg,” an all-beef frank so plump it’s hard to remove it from its cartoon-covered box. After a meal of hot dogs, fries, burgers and “Supershakes,” expect to literally roll yourself home. 6363 N Milwaukee Ave (773-763-0660). Sun–Thu 11am–1am; Fri, Sat 11am–2am. Average main course: $8.