South Beach Wine & Food Festival
A stalwart that's served hearty portions since Prohibition
From pastas and ultra-tender veal limone, to some of the best tiramisu in the city, Bruna’s has all things Italian pretty well covered. The Oakley Avenue mainstay (located in the REAL Little Italy) has been serving the hungry folks of Chicago since 1933, and it shows. Stop in for an authentic experience of roast chicken made with an old-school, original recipe (served only on Sundays) and more than enough wine to make this a regular thing.
A standby for creative Tuscan plates and an extensive Italian wine list
As one of the first Tuscan-inspired restaurants to open in Chicago, Coco Pazzo has consistently churned out a solid mix of classic and contemporary eats every bit as delicious as they are simple since the '90s. Dig into homemade, stick-to-your-ribs potato gnocchetti tossed with tomato sauce, buffalo ricotta, and basil, or sink your teeth into Florence’s famed bistecca, a 40-ounce wood-grilled porterhouse for two that’s sliced tableside. Then cap off your meal with something sweet like house-made gelato or panna cotta with huckleberry sauce and caramelized citrus zests.
Its name means "little dream," and its lush garden patio is heavenly
From homemade pastas and hand-tossed pizzas, to a thorough, Italian-only wine selection some 400 varieties strong, this "little dream" on Halsted Street checks all the mustachioed boxes for what it means to be a great Italian restaurant. Try the signature ravioli stuffed with four cheeses, drizzled in a Marsala glaze and butter, and finished with pine nuts and Parmesan curls for something straightforward and satisfying. Get your hearty protein fix via the rosticciana (braised beef short ribs with squash puree, red wine, and veggies). Also, the outdoor area is easily one of the most romantic patios in town.
Bustling, bi-level spot for groups to share multiple plates
Unlike most of the restaurants on this list, the always hopping Quartino ditches massive portions in favor of smaller, shareable plates. To get the full experience, enlist a couple (OK, maybe five) dining companions to help you eat your way through an assortment of meats and cheeses; pancetta-wrapped dates; veal meatball sliders; braised pork-stuffed ravioli; penne alla vodka; fried calamari; and, most importantly, zeppole.
An approachable joint with homemade pasta specialties and live jazz
This cozy, neighborhood-y spot offers upscale food in a decidedly casual setting: a juxtaposition we’re all about. Whether you’re here for a date night or just a good meal out with friends, it’s great for savory, slow-cooked veal osso buco with red sauce atop a mini meat lasagna, linguini tossed with clams and garlic in a white wine sauce, lobster-stuffed ravioli, and comforting minestrone. Live jazz music on Tuesday evenings makes it a go-to for an intimate weekday night out.
The uncontested gold standard for (pricey) Italian fine dining
When it comes to Italian fine dining in the heart of Chicago, nothing touches Tony Mantuano’s Michelin-starred Spiaggia. The Mag Mile standby has a light, airy aesthetic, tables with views of Michigan Avenue, and a philosophy that draws from the Italian concept of "sprezzatura," aka nonchalant elegance, aka ditch the jackets, revel in caviar and burrata, gnocchi showered in black truffles, perfectly marbled ribeye that's been dry-aged for 45 days, and a deconstructed tiramisu. For a more wallet-friendly experience, the adjacent sibling café doles out equally refined dishes in a more casual setting, a perfect midday shopping escape.
The ideal hub for the flavors of northern Italy
Hearty Northern Italian fare is the name of the game at this Piedmont-focused spot nestled in Logan Square -- that means truffles, cream, and eggy pastas on the menu. Every meal here should begin with a selection from the remarkable wine list and end with a blood orange crostata with vanilla cream. Try dishes like the polipo, a crispy octopus confit, pork belly, and warm bean salad dish; plin (or “pinched") ravioli filled with La Tur, a three-milk cheese, and tossed with Parmesan and a thyme-butter sauce; and prosciutto-wrapped rabbit loin.
A North Side restaurant that knows its regional Italian food
Cozy, charming, and entirely devoid of trendiness or pretension, this trattoria is the place to go for well-executed and wholly authentic Italian. Vitello tonnato (poached veal carpaccio with tuna and caper sauce) and burrata with prosciutto shine among the antipasti options, and saffron risotto with veal and ricotta meatballs in osso buco sauce, pappardelle with porcini mushrooms and white truffle sauce, and veal saltimbocca also won’t disappoint. The owners even opened up a 45-seat wine bar, Riccardo Enoteca, directly across the street to please the crowds.
Sophisticated menus for Italian seafood that change daily
One Off Hospitality Group’s dapper restaurant inside the Thompson Hotel gives Gold Coast locals and visitors a go-to Italian spot for ultra-fresh seafood and flawless pastas. Start the day with pastries paired with black currant jam, vanilla honey, or fior di latte, or end it with octopus carpaccio, lobster spaghetti, and a scoop of cannoli gelato. If you're short on time, refresh with a stiff, Amaro-based cocktail and light snack from the good-looking bar, dubbed Salone Nico.
A classic supper club with live violinists and wall-to-wall retro charm
This North Side Italian gem with tuxedo-clad servers, tables with fresh flowers, and violinists serenading diners by candlelight has withstood the test of time since 1969 (or so it's estimated). Come for the ambiance, but also for the complimentary, to-die-for pizza bread and straightforward classics like chicken Vesuvio sauteed in a garlic and oregano white wine sauce, tender veal saltimbocca, and baked Alaska that’s flambéed tableside for a taste of time machine magic.
Roman-style cuisine with terrifically varied meatballs
A relative newcomer to the Italian dining scene, this Andersonville restaurant has become something of a mecca for meatballs. While the Roman-style, hand-rolled pastas and wood-fired pizzas here are simply delicious, people keep coming back for the balls, or "polpette" on the menu. Get yourself an Italian-inspired craft cocktail and dive into whatever meatballs strike your fancy: braised beef cheek, veal sweetbread, spicy pork belly, chicken and pistachio, and lamb merguez-style sliders. Be sure to add a fried egg to your order of balls.
A chic, brick-accented spot inspired by red-sauce joints of the 1950s
The B. Hospitality guys (The Bristol, Balena, and Nonna's) opened the doors to their sprawling Randolph Street restaurant back in 2015 and have been serving up well-executed takes on mid-century, southern Italian cuisine ever since -- even with a menu overhaul leaning toward lighter, seafood- and veggie-focused fare a year later. The dining room's old-school vibe -- complete with crimson banquette seating, white tablecloths, and black-and-white photos -- invites diners to try pasta dishes inspired by the classics like rigatoni, in which the ricotta-topped pasta covered in a pork neck gravy is accompanied by spicy fennel sausage and fluffy meatballs.
A stylish spot great for walk-ins
Influenced by her world travels and family heritage, chef Sarah Grueneberg -- a Top Chef and Spiaggia vet -- takes a modern approach to traditional Italian cooking, and it's served her well: She took home the James Beard Award for Best Chef in the Great Lakes Region in 2017. The lauded restaurant's house-made pasta roster includes wok-fried arrabbiata with gulf shrimp, pecorino-showered cacio whey pepe, and family-sized portions of ragu brimming with fusilli, sausage, meatballs, and lamb shank. Also, they always reserve some room for anyone walking in.