With Taylor Street between Ashland and Morgan as its epicenter, Chicago’s Little Italy has undergone major changes over the last several years. What hasn’t changed, though, is it’s where my and my family’s roots are. We have our ideas on the best restaurants in Chicago Little Italy, as well as our favorite drinking establishments, and they range from mainstays that have been around for decades to new(er) kids on the block. Because I lived there for most of my life, I’m often asked about the best places to eat and drink in Little Italy. Here are my picks:
Best for a casual, sit-down meal: Pompei Little Italy. This is a Taylor Street institution that originated more than 100 years ago. Today, it is an enormous cafeteria-style, Italian-American eatery and my go-to for comfort food. The menu has expanded well beyond the original pizza and bread to include items such as fried calamari, eight-finger cavatelli, and pepper and egg sandwiches (the best in the city, as far as I’m concerned). Pompei is an excellent place to have a family meal in a relaxed environment and not have to break the bank.
Best spot to watch the game: Vintage Lounge. As the name would imply, Vintage Lounge aims to recall an earlier time. The mahogany decor, exposed-brick walls, and wrought iron accents throughout the expansive space are reminiscent of and inspired by the 1920s. There is nothing old-fashioned about the food, drinks, and entertainment, though. Vintage offers a full restaurant menu, as well as half-off bar food items; an array of beers and top-shelf liquor; specialty cocktails; and frequent drink specials. With seven televisions and four projection screens inside the bar, and three televisions out in the beer garden, “the game” is sure to be on, whether you stop in on a Sunday Funday or a on different day of the week. Vintage Lounge also is an excellent option for fans heading to Chicago Blackhawks or Chicago Bulls games due to its close proximity to United Center.
Best sweet treats: Scafuri Bakery. Originally opened in 1904 by Italian immigrant Luigi Scafuri as a tribute to his native culture, the bakery was kept open by family members for the next 100 years. In 2007, Luigi’s daughter, Annette Mategrano, at age 90, decided to close up shop. Thankfully, Annette’s great-niece, Michelle, decided to continue the family tradition and began work to renovate and re-establish Scafuri Bakery, and it reopened in May of 2013. Michelle and her team have maintained the same quality of products using the same century-old family recipes while incorporating modern offerings like free Wi-Fi and live jazz. As for the treats, choose from doughnuts and cookies to more traditional Italian goodies like sfogliatelle and cuccidati.
Best place to go without the kids: Three Aces. I make it no secret that Three Aces is my favorite place in the entire city of Chicago. Since it is in Little Italy, naturally I had to include it on this list! One thing I love most about this “rockabilly gastropub” is its tagline: “The Italian countryside meets the American farmhouse… in Keith Richards’ basement bar.” The description is fitting and it’s the main reason I suggest leaving the kids at home. Mom and Dad need the chance to fully enjoy the outstanding beer and liquor selection at Three Aces, consisting mainly of American craft beers and spirits. While the setting definitely leans more toward the bar atmosphere, it’s the food at Three Aces that steals the show. The farm-to-table menu is divided into four main sections (Farm, Mill, Sea, and Barn), features local ingredients, and changes seasonally. The menu also includes year-round staples like pizzette (personal pizzas) and bolognese fries (one of my favorite dishes). Also, the outdoor patio at Three Aces is one of the best in the city.
Can’t pick just one place to try? Fear not! Come to Chicago Festa Italiana, the annual celebration of Little Italy’s history and heritage. The street festival runs August 14-17, 2014. Along with the establishments I’ve chosen here as my favorites (as well as many others from the neighborhood), there will be activities like grape stomping and a meatball-eating contest; live music on three stages; and carnival rides for the kids. Come back to the old neighborhood!