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The Ultimate Chicago Chow Down: Pies, Dogs, and Italian Beef You'll Drool Over

The Ultimate Chicago Chow Down: Pies, Dogs, and Italian Beef You'll Drool Over

Your guide to eating your way through Chicago (Photo: Jose Luis Stephens/Radius Images/Getty Images)

Oprah. Architecture. Lake Michigan. These are just a few things often associated with Chicago. But in recent years, this Midwestern metropolis has succeeded in adding another three words to that list: “culinary hot spot.” 

The fact that Chicago beat out New York to host the 2015 James Beard Awards, the Oscars of the epicurean world, is proof that the buzz surrounding Chi Town’s avant-garde restaurant scene has reached fever pitch. However, even as Chicago completes its transformation into a renowned foodie destination, locals continue to embrace the old-school scene they love — and that visitors often overlook.

On a recent vacation to the Windy City I got my first taste of one of those only-in-Chicago experiences when a friend insisted I try an Italian beef, a sloppy sandwich of shredded meat seasoned with Italian spices. For locals, it’s a traditional go-to meal. For me, the Italian beef was a revelation, one of those rare foods so delicious it was all I could think about (full disclosure: I scarfed down three in two days).


Food writer/TV host Catherine De Orio helps us navigate our way through Chicago’s food scene (Photo: Aaron Rasmussen)

My discovery had me wondering: What other magical meals had I been missing out on during all my past trips here? To answer that question, I enlisted the help of Catherine De Orio, food writer and host of the popular Chicago-area dining show Check, Please!, to give me a sample of the best fare her hometown has to serve up.

Related: Cheat Sheet: Chicago



The food is no joke at Johnnie’s… and neither is the line (Photo: Aaron Rasmussen)

A line snakes around this no-frills takeaway stand even before it opens the door for lunch. Johnnie’s menu is limited, which is a good thing since big crowds translate into precious little time to dilly-dally with decisions at the register. Luckily, an Italian beef is a foolproof selection.


A good italian beef sandwich will change your life (Photo: Aaron Rasmussen)

INSIDER TIP: Catherine De Orio recommends getting the Italian beef with sweet or hot peppers and requesting that it be “dipped” (or “extra juicy”), meaning it’s dunked in a special juice concoction flavored with secret spices. 7500 W. North Ave., Elmwood Park; 708-452-6000

Gene’s & Jude’s

You’ll find great hot dogs at Gene’s & Jude’s. Ketchup, however, is another story (Photo: Aaron Rasmussen)

It turns out Chicagoans take their hot dogs very seriously. De Orio explains that a true Chicago-style dog is steamed and served on a poppy-seed bun with tomatoes, white onions, relish, sport peppers, celery salt and a dill pickle spear. She suggests that newbies check out the scene at the famous hot dog stand Gene’s & Jude’s


We double-dog dare you to enjoy this Gene’s & Jude’s “Double Dog” (Photo: supafly/Flickr)

INSIDER TIP: De Orio says that in Chicago, ketchup on a hot dog is a huge faux pas and should always be shunned. In fact, Gene’s & Jude’s doesn’t even offer the condiment to its customers. 2720 River Road, River Grove; 708-452-7634

Watch: Another Chicago Hot Dog institution, Superdawg

Wiener Circle


Get a hot dog with a side of insults (Photo: Gazelle Rivera/Flickr)

For an option closer to downtown Chicago, Wiener Circle is a unique place to get a good dog. The joint is wildly popular late at night, but beware: Acerbic servers here are famous for hurling distasteful insults at patrons.


Chicagoans endure biting insults to be able to bit into this (Photo: Benny Mazur/Flickr)

INSIDER TIP: De Orio says going to Wiener Circle is an experience to be relished and highly encourages talking back to the sassy staff. 2622 N. Clark St., Chicago; 773-477-7444

Lou Malnati’s


(Photo: Aaron Rasmussen)

Lou Malnati’s Pizzeria has been around since 1971, and though it now has around 40 locations, it’s still revered for serving up one of the most authentic Chicago-style deep-dish pizzas in town. The secret to its success? Malnati’s pies are made with a rich, buttery crust.

INSIDER TIP: When talking about a deep-dish pizza, always refer to it as a “pie.” And though pepperoni is a perennially favorite topping, Malnati’s menu warns that diners “can’t have a true Chicago-style pizza without sausage.” Various locations throughout Chicago


La Scarola


A (crowded) Chicago institution: La Scarola (Photo: La Scarola Italian Restaurant/Facebook)

Loud and lively, La Scarola is a Chicago institution that is always packed, thanks to its heaping dishes of pasta with meatballs, eggplant parmigiana and other Italian mainstays. De Orio says that even Chicagoans feel as if they’ve discovered something special when they dine in this cozy hole-in-the-wall restaurant with its framed photos of celebrity fans, including Cindy Crawford and Johnny Depp, that cover the walls.

INSIDER TIP: Be prepared to wait for a table and don’t complain, says De Orio. She adds that as a reward for good behavior, one of the restaurant’s owners, Armando, often downs tequila shots with his patient patrons. 721 W. Grand Ave., Chicago; 312-243-1740

Pan Hellenic Pastry Shop


(Photo: laschofield2001/Flickr)

Chicago is well known for its many ethnic neighborhoods, and Greektown in the West Loop is one of the best for food. Pan Hellenic Pastry Shop (conveniently located just across from the National Hellenic Museum) boasts the most varied selection of sweets in the area. Unsurprisingly, the baklava, drenched in the shop’s signature honey syrup, is the best seller, but De Orio says an order of Louie’s Cookies will make you shout “opa!” Named after Pan Hellenic’s owner, these decadent fudge-filled confections are made of chocolate, walnut and meringue and come two to an order.

INSIDER TIP: In-the-know folks with a sweet tooth hit Pan Hellenic on Saturdays, the only day it makes its beloved loukamades — fried dough dumplings drenched in honey and dusted with cinnamon and crushed walnuts. 322 S. Halsted St., Chicago; 312-454-1886  

Related: Chicago: Three Days, Three Ways 

Gibsons Bar & Steakhouse


The perfect choice for the “meat and potatoes” crowd (Photo: Gibsons Bar & Steakhouse/Facebook)

Midwesterners are often said to be steak-and-potatoes people, which could explain why Gibsons Bar & Steakhouse is so popular. A more likely reason, says De Orio, is that this classic fat-cat restaurant serves huge portions, from 48-ounce porterhouse steaks to its famous 20-ounce martinis.

INSIDER TIP: A side dish at Gibsons can practically be a meal in itself. No matter how hungry you are, don’t over-order, and plan to share what you do get with the table. Anyone hankering for a little surf with the turf can request menu items from the seafood restaurant Hugo’s Frog Bar & Fish House, since the two share a kitchen. 1028 N. Rush St., Chicago; 312-266-8999




You may find Sixteen to be a perfect “10” (Photo: Rebecca Peplinski/Flickr)

Nothing beats the views of Chicago’s stunning skyline, packed with  architectural masterpieces. To sample some of the country’s finest food along with the delectable scenery, De Orio notes that Sixteen, located on the 16th floor of the Trump International Hotel and Tower, recently gained a second Michelin star under the guidance of Executive Chef Thomas Lents. It’s now become one of the spots that both well-heeled residents and tourists head to for an unforgettable gastronomic experience.


Pricey, but worth it (Rebecca Peplinski/Flickr)

INSIDER TIP: The tasting menu, which may include courses like smoked foie gras, razor clams and sweetbreads, or prime filet of beef and broiled eel, is a splurge but worth every penny. Be sure to request a table by the window when making reservations. 401 N. Wabash Ave., Chicago; 312-588-8030


Calumet Fisheries


A longtime South Side treasure: Calumet Fisheries (Photo: Eric Allix Rogers/Flickr)

Run for almost 70 years now by the Kotlick-Toll family, this old-school gem is literally a shack of a building, but well worth the trip to the South Side. Calumet Fisheries is one of just a handful of smokehouses still in existence in Illinois, and locals are smitten with the takeaway restaurant’s fish that’s marinated in brine and cooked over an oak-log-fed fire.


Deep-fried poetry (Jonathan/Flickr)

INSIDER TIP: Calumet Fisheries is takeout only, so be prepared to eat in the car. Trivia buffs should note that the nearby 95th Street Bridge is the same one that Dan Aykroyd and John Belushi leaped across in the beginning of the 1980 movie The Blues Brothers. 3259 E. 95th St., Chicago; 773-933-9855 

Chicago Gourmet


A can’t-miss for Chicago Foodies: Chicago Gourmet (Photo: Chicago Gourmet/Facebook)

De Orio insists that those lucky enough to be in town in late September buy tickets for Chicago Gourmet. Millennium Park in downtown is the setting for the three-day festival, which will feature top-notch wines and gourmet food samples from dozens of the city’s best chefs and restaurants. Chicago Gourmet will also include various separate events, like the Hamburger Hop burger-making competition and Grand Cru, an afternoon of culinary treats whipped up by James Beard Award-winning chefs.

INSIDER TIP: The Dine Around program offers gourmands the chance to take their receipts from five participating restaurants and exchange them for a free one-day pass to Chicago Gourmet.

Aaron Rasmussen is a Brooklyn-based writer who has gained new respect (and quite a few extra pounds) for Chi-town and its culinary scene.

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