Scott Harris, the James Beard Award-nominated chef behind Purple Pig, tackles Italian-style tapas at this Taylor Street spot. Meals start with cheeses and cured meats, then builds to giant raviolis, béchamel pizzas, and grilled swordfish. Purchase a bottle of wine on-site ($7 corkage fee) or grab a house-infused vodka at the bar, made from 180-year old refurbished barn wood.
This Chicago chain prides itself on generous portions at reasonable prices. Settle in for a bowl of housemade pasta—you can pick the pasta and the sauce for $10.95. Keeping with the oversized theme, Leona’s Darn Good Burger is a half-pound of 100% ground steak served on a house-baked pretzel bun.
A Restaurant Row pioneer since 1981, Mart Antony uses family recipes passed down by generation. Veal chop marsala, sausage, peppers, and potatoes, and a signature braciole (two filet tenderloins rolled and stuffed with cheese and prosciutto, topped with marinara) highlight the menu.
Named one of the nation’s Top 50 Best New Restaurants 2012 by _ Bon Appétit_, Balena is located across the street from Steppenwolf Theatre. The restaurant’s menu focuses on thin-crust pizzas and is complemented by Amaro cocktails, rated on a scale of 1–10 for bitterness.
Ombra offers a taste of the Triveneto region of northeastern Italy for a lot less than a ticket to Venice. Italian wines and tramanzzini (Venetian finger sandwiches) anchor the dinner menu. Ombra was named one of Chicago magazine’s 20 best new restaurants, in part for its use of faded Italian newspapers as decoration.
With its outdoor patio, Piccolo Sogno won Chicago Reader’s “Best Alfresco Dining” award in 2012. Mature shade trees provide cover outdoor diners, who come to taste Roman-style pork and the restaurant’s seasonal Mediterranean sea bass. Owner and oenophile Ciro Longobardo handpicks more than 400 Italian wines to complement the restaurant’s authentic dishes.
Wednesdays and Thursdays are date nights at RoseAngelis, as parties of two get a shared appetizer, two Caesar salads, two entrees, and a dessert for $49. The restaurant specializes in northern Italian dishes, as well as an aged New York strip steak encrusted in peppercorn and finished with gorgonzola, sautéed onions, and grilled asparagus.
Chef Massimo Di Vuolo’s mantra—“Love for food. Love for life”—was born in his grandmother’s kitchen in Napoli, where he first learned how to share fresh, seasonal dishes. At his Michelin Guide recommended restaurant, chef Di Vuolo’s menu of authentic plates pair with dozens of affordable wines, as well as a seasonal outdoor patio.
Deal or no deal, our editors strongly recommend these businesses based on their reputation, popularity, and quality of service.