Best Date Night Magic Italian Restaurants in Near North Side
5 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.
8.8
La Storia Ristorante is a Gold Coast townhouse restaurant pairing handmade regional Italian pastas, wood-fired pizzas, and an extensive wine list with white-tablecloth polish. Diners come for rich seafood pastas, long-form dinners, and a room that feels suited to anniversaries and special nights out more than quick plates of red sauce.
Must-Try Dishes:
Squid Ink Seafood Pasta, Cioppino with Mixed Shellfish, Arugula Pizza
What Makes it Special: Townhouse Italian dining with handmade pastas, deep cellar, and polished service.
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.
Set on the 12th floor of The Ritz-Carlton, Torali blends a modern steakhouse with Italian pastas and sweeping city views. It’s more about polished ambiance, cocktails, and composed plates than rustic red-sauce comfort, drawing hotel guests and special-occasion diners.
Must-Try Dishes:
Torali Mafalde Bolognese, Pappardelle Bolognese, Prime Flat-Iron Steak Frites
What Makes it Special: Ritz-Carlton steakhouse with Italian pastas and 12th-floor city views.