Bring the Windy City to Your Town: 7 Chicago-Style Menu Items to Consider

words Alexa Wang

Chicago doesn’t come by its nickname, “The Second City,” happily. From its founding as a swampy 19th-century trading outpost, Chicago lived in the shadow of its bigger cousin to the east — New York City. 

Yet Chicago has a rich history and tradition all its own. And nowhere is this more evident than in its unique, sometimes-maligned culinary scene.

Windy City food

Just like New York-style pizza or Philly-style sandwiches, elements of that culinary scene transcend the Windy City. The words “Chicago style” mean something to the average American diner — whether they bring to mind deep-dish pizza, colorfully dressed sausages, pierogies, or saucy barbecue ribs.

You don’t have to go all-in on a Chicago-themed restaurant concept to take advantage of the Windy City’s gastronomical heft. You can selectively pepper your menu with odes to the city, drawing in diners eager for a taste of the place for far less than the price of a plane ticket.

Start with these seven affordable, easy-to-make options.

1. Chicago-Style Cracker Crust Pizza

Er, not deep dish?

We’ll get to that in a minute, but first, a nod to the true-original Chicago-style pizza.

True Chicago pizza fans know where in the Windy City to find cracker crust pizza. Elsewhere, the most faithful replication probably comes courtesy of Dallas-based Vandelay Hospitality Group, whose Drake’s Hollywood and D.L. Mack’s restaurants serve up tremendous pies in North Texas.

2. Deep Dish Pizza (The “Other” Chicago-Style Pizza)

You asked for it, you got it. The “other” Chicago-style pizza is actually a fairly recent invention, and it’s definitely a love-it-or-hate-it thing. Some innovative restaurateurs have moved away from calling it “pizza” at all; they prefer “pies,” and they have a point.

3. Italian Beef Sandwich

Don’t tell your friends from Philly, but an Italian beef sandwich is basically a more flavorful, slightly more elevated cheesesteak — without the traditional Cheez Whiz, mercifully.

The filling is also super-easy to make in bulk and keep hot. It’s sirloin or top/bottom round cooked long enough to render the signature jus, which goes back in later and is responsible for the product’s unmistakable mouth-wateringness. Top with sauteed peppers and onions plus the cheese of your choice (Swiss is traditional but cheddar works fine) and house in a sturdy hoagie roll. Viola.

Windy Chicago food

4. Chicago Dog (Chicago Red Hot)

The classic Chicago Dog is just a tad more colorful than your standard hot dog. Every Windy City hole-in-the-wall seems to have its own take, but the basic blueprint is:

  • A poppyseed bun
  • An all-beef dog
  • Some chopped onions
  • A few tomato wedges
  • A pickle slice
  • Some yellow mustard
  • Some relish
  • A spicy pepper or two (banana peppers work fine)

It’s cheap, it’s straightforward, and you can churn out a whole bunch of these during your lunch rush. Why not?

5. Pizza Puffs

Yeah, it’s basically a handmade Hot Pocket. No, you won’t get sued. At least, not if you stick to the line that it’s a “Chicago-style pizza puff,” or perhaps “mini-calzone.” Because that’s what it is.

6. Buttermilk Donut

If you’re running a cafe-style joint or have a breakfast menu, add Chicago-style buttermilk donuts to your lineup. They’re super-easy to make — the recipe isn’t much different from your standard non-buttermilk donut — and the taste experience is different enough that you’re sure to create some new fans.

7. Jibarito Sandwich

Remember KFC’s Double Down Sandwich, the one where the buns were fried chicken filets? The jibarito is basically that, except actually good and marginally healthier. 

The “buns” here are plantain slices, and the filling is typically flank steak, tomato, onion, garlic, mayo, and Swiss cheese. You don’t have to hew to the letter of the recipe though; this is the type of sandwich where creativity comes in handy. Just make sure your patrons have forks and steak knives handy.

Make Chicago Your Own

More than a few successful restaurant concepts owe their success to Chicago food and drink traditions. But we’ve already seen that you don’t need to open a deep-dish pizza joint or sausage emporium to bring a taste of the Windy City to your dining establishment.

You can claim Chicago-style cooking as your own without going all-in. Whether you add a distinctive take on Midwestern flatbreads, an upmarket take on the old-school Chicago dog, or simply add Heileman’s Old Style to your draft list, your restaurant will be stronger for it. 

Here’s to making Chicago your own — however you choose to.

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