Windy City Pizza in Delray Beach offers authentic tastes of Chicago

Windy City Pizza on West Atlantic Avenue

You don’t have to be from America’s Second City to enjoy the culinary specialties offered at this small eatery on Atlantic Avenue, a few blocks west of Downtown. Here, pizzas with cracker-thin crusts; hot dogs with neon relish and yellow mustard, among other toppings; and savory Italian beef sandwiches, delight diners’ palates.

By Alan J. Wax

When I recently asked my neighbor Mike Kaplan to join me for lunch at Windy City Pizza on Atlantic Avenue near downtown Delray Beach, he jumped at the invitation.

Mike, you see, is a born and bred Chicagoan. I’m an ex-New Yorker.

Inside, walls decorated with Chicago sports memorabilia.

But after we entered this tiny spot – it seats just 24 – he passed on the pizza, a thin-crust pie known as a tavern pizza, and instead opted for the Italian beef sandwich ($11.85).

“Gotta have the Italian beef,” said Mike as we sat at table next to the counter, close to Eric Lamb, the 40-year-old chef who took over ownership of the restaurant with several relatives in mid-2020 from its founders. Lamb, who worked in the catering business before joining his relatives in the new venture, grew up in Chicago’s Wrigleyville neighborhood and is well-acquainted with his hometown’s cuisine.

“Do you want it dipped?” asked our server, Lamb’s spritely mom, Shelly Walker. Of course, Mike replied. I followed suit. Dipped means that the sandwiches, overflowing with slices of the tender, juicy Italian-spiced top round roast from Fontanini, a Chicago purveyor of meats to restaurants now owned by Hormel, had been dunked into au jus prior to serving.  The beef is topped with giardinara (picked and marinated chopped vegetables) and bits of jalapeno peppers and served in a French-style roll from Chicago’s Turano Bakery,

Lamb, who lacks a full kitchen, buys his beef from Fontanini, cooked and sliced and packaged in vacuum-sealed plastic wrap.  Lamb says he adds his own seasoning to the factory-made au jus.  (I was surprised it was not cooked on premises, but then neither is the pastrami and corned beef that so many diners order and enjoy at Jewish-style delis.)

Our sandwiches arrived in red plastic, wax-paper-lined baskets, with a small black cup of more au jus on the side, accompanied for an extra $1 at lunch by a mound of crispy French fries and a beverage (Diet Pepsi for me).

“If this were a real Chicago place they’d have Pabst Blue Ribbon and Falstaff,” said Mike, referring to beers that once were staples of beer drinkers in the Second City. Mike passed on the two Chicago-produced craft beers on the menu, 312 Urban Wheat Beer and IPA, both from Goose Island, opting instead for an iced tea.

Italian Beef Sandwich.

Thin-crust sausage pizza.

Chicago Hot Dog with fixings.

Windy City’s garlic bites.

I gently handled my wet, beef-filled roll, hoping it would stand up to its gravy bath.  It did. I took a bite and was overwhelmed by the delicious flavors oozing into my mouth. Yes, it was a tad salty. Mike agreed. But we nevertheless devoured our lunches and went through tons of napkins.  I was barely half through when I noticed that Mike had virtually inhaled his sandwich and was chatting up Lamb about their native city and Super Bowl games past.  The restaurant’s rust-hued and grey walls are adorned with sports memorabilia from the Chicago Bears football team and the Chicago Cubs baseballers, as well as Illinois license plates from an earlier era.

What of Windy City’s other offerings? I tried a few over several visits, though not the deep-dish pizza ($32.99), which takes an hour to prepare and serves four. Locals from Chicago know that the deep dish is mostly for tourists.

Among the other offerings I tried was the Chicago Hot Dog ($5.97). My mouth was dancing as I tasted its bold flavors and textures. Here, this hot dog, which originated during the Depression, is an all-beef Vienna brand sausage (a Chicago staple) that arrives in a warm poppy seed bun and is topped with yellow mustard, chopped white onions, neon green sweet pickle relish, a dill spear, tomato slices, pickled sport peppers and a dash of celery salt. For those who only are acquainted with hot dogs topped with mustard and sauerkraut or red onions in tomato sauce, don’t knock it ‘til you’ve tried it.

And let’s not forget about Windy’s City’s namesake product. The folks at Windy City Pizza make their pizzas with a cracker-thin crust with a slight crunch and they’re topped with a sweet tomato sauce and cheese and other toppings all the way to the edge. The pies, available in several sizes – 11, 14 and 16 inches – are cut into squares instead of wedges and can’t be folded.

Thin-crust Chicago pizza pre-dates the deep-dish variety many of us associate with the city known as the hog butcher to the world. Unlike New York-style pizza, the dough for Chicago’s thin crust version is rolled, not tossed, and cooked much longer to ensure a crunch. Chicago pizza historian Peter Regas, author of the blog,, says square-cut pizza was born in the bars of Chicago’s South Side, where taverns developed a pizza that was less bready, a bit saltier, and could be cut into squares  and served on napkins. It was offered to patrons for free, no doubt to keep customers drinking. Regas says pizza didn’t catch on in Chicago until the early 1940s, after the end of Prohibition. Deep dish pizza may trace its origin to the 1940s, but it did not gain popularity until the opening of Pizzeria Uno in 1955.

Back to the present at Windy City Pizza. I ordered an 11-inch pie with Italian sausage ($10.25). It arrived steaming in a dimpled black pan. It was less crisp than anticipated (it crisped up when reheated at home the next day). The bright red sauce had a nice, sweet zing and the slices of Chicago-style Italian sausage, smothered by cheese, were loaded with fennel. My dining companions ordered different pizza variations, each saying it was good pizza, but nothing special relative to other pizza found in and around Delray Beach.

Meanwhile, a carb-averse friend who joined us enjoyed a humongous Caesar salad with chicken ($12.97).

Garlic bites, small, soft, fried garlic rolls, provided gratis, offered a different spin on the traditional garlic knots dripping with garlic and butter that most Italian eateries serve. They were addictive.

Some offerings, such as salads and chicken wings, weren’t on the menu under Windy City’s prior owners, Ralph Maiolo, a barber from Port St. Lucie, and his son, Kye, who opened the eatery in 2016 in a storefront that was once Mamma’s Pizza Co. Lamb, who had been working in the catering business in South Florida prior to joining with his relatives to buy Windy City mid-pandemic from its founders, expanded the menu.

Based on conversations I had with Chicagoans that I met at Windy City, I’d have to say the pizza and the sandwiches are the real deal.  Moreover, the folks working at the eatery are friendly and attentive.  In sum, the Second City specialties here are first rate.

Windy City Pizza

401 W. Atlantic Ave., Delray Beach, 33444

(561) 266-2811

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