Best Business Lunch Power Players Italian Restaurants in Near North Side
3 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Osteria del Pastaio
Gold Coast osteria focused on fresh pasta, truffle dishes, and wine.
Notable Picks
8.5
Osteria del Pastaio brings a more polished, wine-driven take on Italian cooking to a side street just off the Magnificent Mile. Fresh pastas, truffle-forward specials, and a serious wine list make it a frequent choice for Gold Coast date nights and lingering dinners.
Must-Try Dishes:
Housemade Tagliatelle, Pappardelle Bolognese, Pecorino al Tartufo Nero
What makes it special: Gold Coast osteria focused on fresh pasta, truffle dishes, and wine.
8.2
Part of the Francesca’s group, this Chestnut Street location has served rustic trattoria fare to the Gold Coast since 2009. The menu centers on pastas, roast chicken, and hearty antipasti that work as well for neighborhood regulars as for hotel guests and pre-shopping dinners.
Must-Try Dishes:
Pollo Arrosto Romana, Pollo Milanese, Rigatoni alla Vodka
What makes it special: Gold Coast trattoria pairing rustic pastas and roasts with steady service.
#3
Labriola
8
Vibes:
Family Friendly Favorites
Group Dining Gatherings
Business Lunch Power Players
Pet Friendly Paradise
Award-winning deep dish and thin-crust pizzas anchor this spacious Magnificent Mile Italian eatery, blending European tradition with American passion. Dog-friendly patio and versatile menu make it a neighborhood anchor.
Must-Try Dishes:
Award-Winning Deep Dish, Margherita Thin Crust, Pan Pizza
What makes it special: Award-winning pizza in a vast space right off the Magnificent Mile