Best Group Dining Gatherings Italian Restaurants in Near North Side
3 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Volare Ristorante Italiano
High-volume, classic Streeterville trattoria serving hearty pastas since 1997.
Notable Picks
8.8
Volare is a Streeterville standby for old-world Italian cooking, tightly packed tables, and big plates of pasta served in a room that’s been humming since 1997. Guests come for house classics like gnocchi alla vodka and seafood pastas, plus a deep Italian wine list that keeps the space buzzing night after night.
Must-Try Dishes:
Gnocchi alla Vodka, Spaghetti Neri al Pesce, Fettuccine alla Bolognese
What Makes it Special: High-volume, classic Streeterville trattoria serving hearty pastas since 1997.
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