It’s no secret that opening a restaurant—and keeping it open—is no easy task. In Chicago, new and hip eateries pop up monthly and can close just as quickly. However, some restaurants stand the test of time, becoming intertwined in the fabric of their neighborhood.

In Chicago’s Little Italy, the neighborhood is packed with local staples that have been around for generations. Rich in culture with spots like the Italian American Hall of Fame and Piazza DiMaggio and home to students at the University of Illinois at Chicago campus, Little Italy also tells a story through its beloved restaurants. 

These seven restaurants, bakeries, delis, and dessert shops have catered to Little Italy residents for decades and represent the rich history in this southwest Chicago neighborhood.

Mario’s Italian Lemonade

Nestled in a small shack on Taylor Street, Mario’s Italian Lemonade has remained virtually unchanged since Mario and Dorothy DiPaolo first opened its serving window in 1954. The stand is hard to miss—it’s painted the colors of the Italian flag and almost always has a long line of eager customers out front.

The popularity of Mario’s could be attributed to their take on traditional Italian ice; it’s considered to be in a drinkable, slushie form and comes with both a spoon and a straw. Mario’s features fruit flavor like banana, strawberry, and cherry, and other limited-time flavors. From May through September, this lighted stand attracts not only Little Italy denizens, but people from all over Chicagoland.

Conte Di Savoia

Since 1948, this deli-grocery store hybrid has been serving the Little Italy neighborhood with Italian dishes and imported groceries on Taylor Street. In its early days, locals would stop by and peruse the wicker baskets out front filled with snails and dried cod fish. Now, UIC students crowd the deli counter for stomach-filling Italian and meatball subs. 

The grocery store inside is stocked with ready-to-cook meals (like the lasagna and frozen ravioli), party trays, and imported olive oils, wine, and coffee beans. With all the ingredients ready on hand, the store will even arrange a picnic basket full of bread, meat, cheese, and wine if you call ahead. 

Tufano's Vernon Park Tap

With many of the prominent restaurants sitting on Taylor Street, Tufano’s Vernon Park Tap breaks that mold on Vernon Park Place. In 1930, Theresa Tufano and her husband Joe DiBuono opened their restaurant next door to their home, serving homemade Italian dishes. Now, the restaurant remains in its original spot run by Theresa’s grandson Joey and his family.

Sticking to the matriarch’s homestyle cooking, Tufano’s has received the “American Classics Award” from the James Beard Foundation and has been featured on Guy Fieri’s “Diners, Drive-Ins, and Dives.” Menu staples include lemon chicken, eggplant Parmesan, and fried calamari. Tip: Tufano’s is old school, so it’s cash only. 

Scafuri Bakery

Nearly every neighborhood has a great bakery, and Scafuri’s is Little Italy’s. Luigi Scafuri immigrated from Calabria, Italy, to Chicago in 1901 and opened the bakery in 1904 as tribute to his Italian heritage. The shop was paramount to the residents’ everyday lives, and Luigi would even hand out bread to families during the Great Depression. Through all the ups and downs of history, Scafuri’s was passed down through generations until a brief closing in 2007. 

However, in 2010, members of the Scafuri family reopened the bakery on Taylor Street. Just as it did in the 20th century, the bakery attracts its loyal customers with baked goods like the lemon ricotta pound cake, Italian cookies, cannoli, and breakfast dishes. 

Jim’s Original

While many landmark restaurants in the neighborhood feature Italian fare, one Polish hot dog stand has firmly planted its roots and stayed a neighborhood fixture for more than 80 years: Jim’s Original. Jimmy Stefanovic moved from Macedonia to Chicago in 1939 and took over his aunt’s hot dog stand on Maxwell and Halsted streets, where and it stayed for decades. 

Jim’s legendary Original Maxwell Street Polish Sausage Sandwich has stayed true to its classic 1940s recipe: Polish sausage on a hot bun with yellow mustard, caramelized onions, and spicy sport peppers. The 24-hour stand is now run by Jim’s family and has relocated to Union Avenue due to UIC expansion. While in a new location, Jim’s Original has stood the test of time. 

The Rosebud

While not as old as some of the Italian staples in Little Italy, Rosebud has certainly cemented itself as a cornerstone in the neighborhood. Over 40 years ago, Chicago native Alex Dana opened the Rosebud on Taylor Street where his authentic Italian comfort dishes attract Chicagoans, tourists, and celebrities alike.

What started off as a single restaurant has expanded to nine locations throughout the city and suburbs, becoming a household name among Chicagoans.

The restaurant has had such an impact on the neighborhood that out front is an honorary street sign naming Taylor Street “Alex Dana Way.” Dishes like the chicken vesuvio, pork chop calabrese, and stuffed artichoke are favorites, but also try the baked ziti—Tom Hanks has called it the best he’s had.

Pompei

One of the oldest Italian restaurants on Taylor Street, Pompei was started in 1909 by Luigi Davino who lived with his family above the restaurant where they baked bread and sold cheese pizza. After Luigi’s sons returned home from World War II, they helped run the shop for years to come. Since then, the business has been passed down through four generations with an expanded menu.

Pompei claims to have started the fast-casual trend in the 1980s, way before it was hip. Customers order their food from the front counter and have the option of 20 signature pizzas (including gluten-free options), appetizers, their “pizza strudels,” pastas, salads, sandwiches, and desserts that are brought to the table.