Al’s Italian Beef

Along with deep-dish and Chicago char dogs, Italian beef completes the trinity of Chicago foods. The concept is simple enough: Take pieces of shredded roast beef marinated for hours, insert them into an Italian roll, dip it into a pool of au jus, and top it with giardiniera (hot peppers). Each one has to be served on a gloriously greasy piece of wax paper. The product, in any case, is not my favorite creation, though it is admittedly essential to the city’s rich culinary history. The heart-stopping, artery-clogging monstrosity might satisfy the strong willed, but some of us might question the cost it comes at. Goodbye sweet lifespan! Classic American, Multiple Locations—River North: 169 West Ontario Street, (312) 943-3222, Regular Al: $5.99.

—Richard Deulofeut-Manzur

Au Cheval

Think of everything you need to start a trendy, contemporary American gastropub. Poor lighting. Check. A subtle blend of slate and brick. Check. A wrap-around bar serving cocktails lifted from episodes of Mad Men. Check. Miscellaneous vintage ephemera. Check. Chopped chicken liver and beef stew? Amidst the ultra trendy celebrity-run restaurants of the West Loop—including Stephanie Izzard’s Girl and the Goat, and Graham Elliot’s eponymous bistro—is a just-surprising-enough twist on traditional Jewish diner fare. The menu was crafted, I suspect, specifically to please Guy Fieri’s palate, and the decor to hide his spikey bleached hair. Foie gras comes either in terrine, cabbage, or with eggs and toast. Fries come topped with mornay sauce and a fried egg. The Kosher dill pickles come on their own plate. Go because it’s not your typical “greasy spoon” diner. Leave with a full belly, a touch of guilt, and grease on your shirt. Contemporary American, 800 West Randolph Street, (312) 929-4580, Entrées: $9–24.

—Colin Bradley

Bongo Room

Tucked into the corner of a residential complex near the Roosevelt Red Line stop, the Bongo Room offers breakfast and brunch to the trendy crowds. Lines start early, even before they open, so don’t hope for anything speedy unless you’re an early bird. Expect American breakfast done right, and with a few twists. It’s hard not to fantasize about the richness of the red velvet pancakes, which are generously topped with their heart-warming vanilla crème. These are hotcakes born for your Instagram account. For the savory eater, the chorizo potato avocado omelette balances the light and hefty without overdoing either. Breakfast, brunch, Multiple Locations—South Loop: 1152 South Wabash Avenue, (312) 291-0100, Average Entrée: $13.

—Richard Deulofeut-Manzur

Chicago Diner

Meat free since ’83—and I think we’re all happy it’s worked out so far. Still serving from its original Boystown location, the Chicago Diner continues to beef up vegetarian and vegan cuisine to the enjoyment of carnivores and non-carnivores alike. Popular on the menu is the Radical Reuben, filled with seitan roast ‘beef’ soaked in beet juice and pickling brine that make the deli flavors jump right out at you with every savory bite. Try the shakes as a hearty pairing to the imitation meat, especially the cookie dough peanut butter vegan shake. If you think you know how dense cookie dough and peanut butter can get, you probably haven’t feasted on this double whammy. Vegan diner, Multiple Locations—Boystown: 3411 North Halsted Street, (773) 935-6696, Average Entrée: $10; Large Shake: $6.99.

—Richard Deulofeut-Manzur

Honky Tonk BBQ

Of all the cuisines to develop in Chicago’s recent history, barbeque has perhaps seen the most progress. With promising newcomers appearing every year, and with a formidable presence from some veterans like Lem’s and Twin Anchors, the BBQ scene has become a difficult one to stay on top of. Honky Tonk, however, is more than just good ribs and pulled pork: This Pilsen smoker is a show as much as it is a restaurant, playing on campy and sometimes kitschy Southern themes that somehow work. Live country music and a fully stocked, saloon-like bar add to the feel, which makes those Viking beef ribs and their sauces just a little bit more savory. Barbecue, American, 1800 South Racine Avenue, (312) 226-7427, Average Sandwich: $8; Average Platter: $13.

—Richard Deulofeut-Manzur

Lao Sze Chuan

A mecca for UChicago students so popular that it might as well be part of the Common Core. Standout dishes are usually those that pack the most heat. An opening plate of spicy cabbage sets the mood—stringy, spicy, and yet somehow refreshing; their boiled beef pot, layered thick with red pepper flakes, produces just as much flare in its flavors as it does in the back of your throat. Don’t worry, though—we’re talking tears of joy here, not pain. After dinner, be sure to drop by Joy Yee’s for bubble tea: a convenient excuse to cleanse your fire-burdened palate. Chinese, 2172 South Archer Avenue, (312) 326-5040, Entrées: $11–14.

—Richard Deulofeut-Manzur

Lou Malnati’s

If there has to be a de-facto rule of pizza eating, it might as well be to find your place and defend it with everything you’ve got. Well, it might not be that severe, but you get the idea. In the world of deep-dish, everyone has his or her camp, whether it’s Giordano’s or Gino’s, or any of the other seemingly ubiquitous Chicago chains. The not-so-secret secret is that the vast majority of deep-dish tastes great, and fairly similar, regardless of location. So what makes Lou Malnati’s so special? It’s simple: It’s not teeming with tourists. Go with friends, order whatever pizza you’d like (the Malnati Classic with sausage is my favorite), and enjoy the local buzz. Pizza, Multiple Locations—Downtown: 439 North Wells Street, (312) 828-9800, Pizza: $6–22 (sizes vary).

—Richard Deulofeut-Manzur

M Burger

Chicago’s very own version of a fast food burger is a small chain started in the back of the kitchen at Tru—a Chicago fine dining institution. It might not have a lot of seating, but their low prices and convenient locations near the Mag Mile make it a keeper. Get the M Burger for a no-frills old-fashioned creation, and always get the fries. It’s hard to say exactly what makes the burger so addictive; maybe it’s the special sauce, the rivers of juice in the patty, or the simplicity of its architecture, but the uncertainty is part of the experience. Either way, the word printed on the bags of fries still holds true: M Burger is “DELICIOUS”. Burgers, Multiple Locations—Magnificent Mile: 161 East Huron Street, (312) 254-8500, Double M Burger: $4.99; Fries: $1.99.

—Richard Deulofeut-Manzur

Molly’s Cupcakes 

Molly’s is the crown jewel of Chicago cupcake boutiques, with a rotating seasonal menu that doesn’t shy away from the bold and brash. Try the apple pie cupcake from their fall menu—a nearly perfect copy of its much larger cousin, though with a fluffier topping. Warning to the wise: bite into one of these gloriously decadent center-filled treats at your own risk; they’ve been known to pack more punch than their flowery colors indicate. It might even help to prep beforehand by limiting yourself to just one cupcake. OK, maybe two. Space is limited and lines can snake out into the street, so expect a wait during peak hours. Cupcakes, 2536 North Clark Street, (773) 883-7220, Center-Filled Cupcake: $3.75.

—Richard Deulofeut-Manzur

Pleasant House Bakery

Dining hall gravy is to be avoided. Not only are the taste and ingredients more dubious than Plato’s happiness algebra, but there is almost nothing you can do to prevent the gravy from sliding over and soaking the pizza and that one leaf of lettuce on your plate. Pleasant House Bakery solves all your problems. Golden, flaky piecrusts enclose a myriad of scrumptious surprises from “Mushroom and Kale” to “Steak and Ale.” The tiny, British, BYOB bakery in Bridgeport also serves up Fish and Chips on Fridays and High Tea on Sunday. Stop off after a day of hard work at Bridgeport Coffee across the street, and bring over some libations from Maria’s, located right next door. They also sell pre-baked savory pies to take home and heat up later to impress your friends. Savory British pies, 964 West 34th Street, (773) 523-PIES, Pies: $8-10.

—Colin Bradley

The Publican

This West Loop “beer hall–esque” creation is known for its meats, oysters, and beer, with touches of everything in between. Chef Paul Kahan, a powerhouse restaurateur in Chicago and winner of the James Beard Outstanding Chef award, has created a menu of mostly small plates that dazzles with the familiar. At The Publican, things are always more than one imagines. Common orders include the pork rinds, with balanced flavors of vinegar and cheese, or any of their carefully selected oysters. But for a real sense of what this restaurant has to offer, consider ordering the surprisingly notable farm chicken. Seasoned to perfection with espelette pepper and Mexican oregano, the chicken shines with its tender and delicate meat. The plate finishes with a bed of fries soaked in the bird’s juices. Chicken has never been so good. Gastropub, 837 West Fulton Market, (312) 733-9555, Plates: $5-30.

—Richard Deulofeut-Manzur

The Wieners Circle

For a classic Chicago dog (aka “red hot”) this is nearly as good as it gets. This famous hotdog joint in Belmont attracts hordes of parading bar-hoppers every weekend, and for good reason: Their mounds of fries and Vienna beef franks are both knockouts. The place has its quirks: a combative staff, a funky location, and a couple of not-so-tasteful secret menu items. But the secret here isn’t the ignominy: It’s the quality of the food. Every ingredient is done as it should be, from the neon-green relish (it really is that color) to the carefully placed sport peppers and sprinkling of celery salt. You’re in Chicago now, so remember to order with all the proper fixins’—ketchup is out of the question. Hot dogs, 2622 North Clark Street, (773) 477-7444, Classic Chicago Dog: $3.10.

—Richard Deulofeut-Manzur