Chicago Italian Restaurants
Chicagoland is full of excellent Italian restaurants—which is no surprise given how many Italians moved to Chicago during the last century. There were only 1,357 Italian immigrants living in Chicago during 1880, but by 1930, the Italian-borne population had swelled to 73,960. These numerous immigrant families gradually became Americanized, but not before seducing Chicago and its suburbs with a love for Italian food.

Chicago’s Little Italy-Heart of Italy

On the Near West Side of Chicago is Little Italy, which is nestled around twelve blocks of Taylor St., east of Ashland Ave. In this corridor, there are plenty of delicious places to get your fill of Italy’s unrivaled cuisine.

Another large enclave of Italian immigrants gathered a few miles southwest of Little Italy in “the Heart of Italy,” which is centered at 24th St. and Oakley Ave. The immigrants here came mostly from northern Italy. Every year they have a two-day Fiesta Pasta Vino. This festival turns the area into ancient Italy, where visitors can indulge in food, wine and song.

Pompei has been making popular Italian fare on Taylor St. since 1909. This restaurant, set up like a cafeteria, lets you watch the cooks make pasta from behind the glass. A well-known hangout for locals as well as police officers, Pompei serves pizza, pizza strudel, desserts and salads to the masses.

For a more upscale vibe, visit Tuscany. This smartly casual restaurant is a warm, comfortable place that makes northern Italian specialties as well as homemade pasta, pizzas, and tender veal. Don’t forget to save some room for dessert.

Francesca’s on Taylor serves the zesty, earthy cuisine of Roma as well as selections from the surrounding areas of Tuscany, Umbria and Lazio. The menu changes daily, but includes pizzas, meats and pastas with seasonal ingredients.

Chicago Loop/ River North

Visitors to Chicago always congregate in this area, which contains some of the city’s highest-profile buildings and companies. It also features excellent cuisine and shopping. No wonder some of the Italian food found here is to die for.

Harry Caray’s Italian Steakhouse is a classy tribute to the legendary Chicago Cubs’ announcer. The building was once home to one of Al Capone’s henchmen, but now serves fine aged steaks and chops in the kind of steakhouse atmosphere only Chicago can serve up. You can also see a huge array of baseball memorabilia here.

Giordano’s is famous for its thick-crust Chicago-style pizzas. These pizzas are made with the crust first, then the cheese, and a savory tomato sauce tops it off. But for additional deep-dish pizza action, you can also try the delectable pies at Gino’s East. In fact, you’re practically required to compare and contrast these pizzas if you visit Chi-town. Of course, the birthplace of the Chicago-style pizza is Pizzeria Uno’s, with Pizzeria Duo right next door. And some people prefer the crispy, buttery crust of a good Lou Malnati’s slice. But remember—it takes a while for these made-to-order pizzas to cook, so expect to wait 35-45 minutes. If you want the authentic Chicago-style experience, top your deep-dish pies with sausage. Note that all of these restaurants have numerous suburban locations as well.

The drinks are the specialty of the house at Osteria Via Stato, with a wine list that includes more than 300 Italian labels. This restaurant serves its food family-style, so everyone shares large plates of the entrées on the table. Crispy thin-crust pies are available too.

Ristorante Quartino offers an authentic everyday Italian food and wine experience with cicchetti, small appetizer-sized servings that closely resemble tapas. The restaurant also seeks to recreate the cultural experience in Italy where wine is cheaper than water by offering exactly that.

The Italian Village Restaurants, famous throughout Chicagoland for its high-quality dining options, gives you three choices at one Loop-based location. The Village is designed like a small Italian town, where customers dine on generous portions of authentic Italian food in cozy booths. At La Cantina Enoteca, you’ll step into what looks like a wine cellar with narrow aisles and tucked-away booths. Customers dine among salt-water fish tanks while enjoying steaks and Italian favorites. Vivere is the most upscale of the offerings, with a contemporary vibe that’s complemented by modern, gourmet cuisine created by chef Drue Kennedy. This world-renowned restaurant, with its perfect wine list, is ideal for a romantic evening or a pre-theater meal.

Spiaggia, widely considered to be the best Italian restaurant in Chicago (no small feat), is the place for sublime, classy Italian dining. Chef and partner Tony Mantuano changes the menu with the seasons so that the food is always absolutely fresh. And every table in the beautiful dining room gets a great view of Lake Michigan.

Club Lucky, a Chicago stalwart for more than fifty years, has never looked—or tasted—better. This genuinely retro-yet-hip restaurant feels like a ‘40s supper club and serves up Sicilian-inspired dishes in a traditional style.

Tuscan flavor is the focus at Coco Pazzo.  This stylish, upscale venue serves highly seasoned yet simply elegant Italian cuisine. The bread gets raves from locals and visitors alike, as do the homemade pastas. And don’t you dare overlook the dessert menu.

Gioco is a pleasant place to bring people for a dinner party. It features a wide range of rustic Tuscan and Umbrian dishes, including homemade pasta and wood-fired thin crust pizzas. To add to the ambience, the restaurant boasts a genuine Prohibition-era speakeasy.

Other Italian dining options abound for the culinary adventurer. Head up to Trattoria Gianni a cozy family-run restaurant that’s hosted a few celebrities and a lot of blues and theater lovers (it’s not far from Steppenwolf, Kingston Mines and the Royal George theater). Across the street is another excellent restaurant, Vinci. For light and authentic Naples-inspired pizza in the Ravenswood neighborhood, don’t miss Spacca Napoli. Premium ingredients, a light crust and hand-extended dough cooked in wood-burning ovens turn these concoctions into works of art. For a more swank Italian experience, head over to the historic Biggs mansion, where high-profile Il Mulino New York features traditional Italian dining, including an outdoor seating area with light fare. WindyCityGuide