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The story begins in 1973, when a 17-year-old Sicilian immigrant and his father made their way to the U.S. and settled in the southern Illinois community of Fairfield. There, they opened a modest pizzeria that has brought authentic Italian recipes to the community for more than five decades.
Over time, DiMaggio’s became a beloved fixture in the area, known for its signature cracker-crust pizza, homemade dough and sweet signature marinara sauce, and has passed from father to son.
“It’s the same pizza we made back then,” says current owner Joe DiMaggio, who started in the family business at age 12 and is the son of that 17-year-old immigrant. Now 45, he and his wife Jennifer have been running the pizzeria for the past 19 years.
Running a family business comes with its challenges, but for this couple, teamwork has been the key to success. “We balance each other out,” Joe explains. “She keeps me level-headed, and we just keep each other going.”
While he spends much of his time in the kitchen, Jennifer handles the social media and customer-facing aspects of the business. “But don’t let that fool you,” Joe says. “She’s very well-versed in pizza making.”
Also involved are the couple’s children, Angelina and Giuseppe, who are the next generation to step into the family business. Angelina, 18, has taken on significant responsibilities, including managing their second location in Flora and making dough for both locations. Giuseppe, 17, works whenever his school schedule allows.
“I’ve told them they’re free to choose their own paths, but right now, they’re both very involved,” Joe says.
At the heart of DiMaggio’s success is its pizza. Their pies are a hit among locals and out-of-town visitors alike. Popular pizzas include specialties like their Super Deluxe pizza (pepperoni, hand-pinched hamburger, bacon, ham, onions, green pepper, mushrooms and green olives) and All Meat (hand-pinched sausage and hamburger, pepperoni, ham and bacon). However, Joe loves to keep his pizza simple.
“If you can eat a pizza plain with just cheese or a single topping, you know it’s good,” Joe says. “Just a simple, easy pizza would have to be it for me. My wife’s favorite would be cheese, while mine would be pepperoni. Those are the basics that a lot of people overlook.”
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DiMaggio’s serves more than pizza, however. Their spaghetti is a crowd favorite, thanks to their rich, flavorful sauce. There is also a variety of sandwiches and pastas available.
The team also keeps things fresh with “pop-up pizzas,” limited-time offerings announced on social media. Some favorites include the baked spaghetti pizza, jalapeno popper pizza and “Chi-Town” pizza, topped with Italian beef and giardiniera.
According to Joe, DiMaggio’s also draws customers from neighboring towns, with some driving up to two hours for a taste of their pizza. This support allowed the business to expand.
In August 2024, the family grew their operation 30 miles north in Flora, opening a new branch in the area when a beloved pizzeria there closed after being in business for more than 40 years. The restaurant coincidentally had the same name.
“We’ve been wanting to [expand] for quite a while, and then the opportunity presented itself,” Joe explains. “They [the owners of the other DiMaggio’s Pizza] were excited to hear that the name will continue. … We just wanted to carry on the tradition.”
The new Flora location features the same signature pizza but has a smaller menu compared to the Fairfield location, focusing on simplicity while the team and location gets established. Joe says the response in Flora has been overwhelmingly positive. “The turnout has been great, and the community has been so supportive,” he adds.
Employing about 45 people across both locations, DiMaggio’s is more than a business. It’s also a training ground for many young locals. DiMaggio’s predominantly employs teenagers, and it is oftentimes their first job. “It’s rewarding to see them grow and learn,” Joe says. “We’re not only providing pizza and good food, we’re also giving opportunities to these kids to learn.”
As they continue to grow, the family remains focused on their core values of quality, tradition and community. “We couldn’t have done this without the support of Fairfield and now Flora,” he says. “Our customers are No. 1, and we’re so grateful for them.”