Best Italian Restaurants in Magnificent Mile & Streeterville (60611)
7 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 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.
#2
Rosebud
8.7
Vibes:
Birthday & Celebration Central
Group Dining Gatherings
Girls Night Out Approved
Brunch Bliss Spots
Since the early 1990s, Alex Dana’s Rosebud on Rush has been a Gold Coast fixture for red-sauce classics, celebrity photos on the walls, and portions big enough to share. Brunch, lunch, and late dinners all lean on the same playbook: robust pastas, chicken parm, and tiramisu in a loud, celebratory dining room just off the Mag Mile.
Must-Try Dishes:
Rigatoni Alla Vodka, Chicken Parmesan, Tiramisu
What makes it special: Long-running Gold Coast institution for oversized red-sauce plates and celebrations.
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.
8.1
Vibes:
Cheap Eats Budget Brilliance
Quick Bites Champions
Hidden Gems Heaven
Family Friendly Favorites
Tucked inside Navy Pier’s food hall, Chef Ciccio channels Ferraro family recipes into Italian beef, meatball sandwiches, and protein bowls built for quick counter-service meals. Locals and visitors hit it for scratch-made Italian-American sandwiches that feel more neighborhood than tourist-trap.
Must-Try Dishes:
Famous Chicago Italian Roast Beef Sandwich, Beef & Meatball Marinara Protein Bowl, Chicken Parmesan Sandwich
What makes it special: Independent Navy Pier counter turning Ferraro family recipes into beef and meatball sandwiches.
#6
Labriola
8.0
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
8.0
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.