Best Date Night Italian Restaurants in Wicker Park & West Town (60622)
6 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
Tortello
Daily handmade pasta crafted using Old World Italian techniques with eggs from a dedicated Wisconsin farm
Notable Picks
#1
Tortello
8.6
Chef Dario Monni's counter-service pasta shop produces some of Chicago's finest handmade pasta, crafted daily with imported Italian flour and Wisconsin farm eggs. The open kitchen lets diners watch artisans shape tortelli, tagliatelle, and bucatini while the signature tortelli di burrata with brown butter and sage has become a destination dish.
Must-Try Dishes:
Tortelli di Burrata, Focaccia with Ricotta & Honey, Cacio e Pepe
What makes it special: Daily handmade pasta crafted using Old World Italian techniques with eggs from a dedicated Wisconsin farm
#2
A Tavola
8.5
Chef Daniel Bocik's converted house has delivered Northern Italian excellence since 1995, with his signature gnocchi in brown butter sage sauce earning a devoted following. The intimate candlelit rooms and ivy-covered patio create one of Chicago's most romantic Italian dining experiences.
Must-Try Dishes:
Gnocchi with Brown Butter Sage, Tonnarelli Cacio e Pepe, Veal Saltimbocca
What makes it special: Nearly 30 years of Northern Italian excellence in a converted home with secluded garden patio
#3
Segnatore
8.4
This Humboldt Park gem elevates classic Italian with creative Midwestern twists like meatballs stuffed with melted scamorza and deconstructed lasagna with garlic mafaldine. The candlelit vintage wallpaper atmosphere and inventive pasta preparations have quickly made it a neighborhood destination.
Must-Try Dishes:
Scamorza-Stuffed Meatballs, Bucatini Carbonara, Porchetta with Prune Mostarda
What makes it special: Creative Italian dishes inspired by folk healer traditions with Midwest-sourced ingredients
8.4
Enoteca Roma is a Division Street standby built around Roman-style comfort food, a deep Italian wine list, and a leafy back garden that feels far from the street. Couples come for long, shared meals built around polenta boards, handmade pastas, and bottles that linger through dessert.
Must-Try Dishes:
Bruschetta Flight, Spaghetti Nonna Giovanna, Tableside Polenta
What makes it special: Authentic Roman cuisine with a magical hidden back patio and connected bakery
8.2
Via Carducci La Sorella brings Calabrian-leaning Italian cooking, deep-dish and thin-crust pizzas, and a long wine list to a warmly lit Division Street dining room. It’s the kind of relaxed, slightly old-school spot where date night can be as simple as sharing a pizza, a bottle of red, and tiramisu.
Must-Try Dishes:
Spaghetti Carbonara, Gnocchi Marinara, Grilled Calamari Calabrese
What makes it special: Authentic Calabrian Southern Italian cuisine with family recipes from the owner's hometown
Vibes:
Family Friendly Favorites
Cheap Eats Budget Brilliance
Quick Bites Champions
Comfort Food Classics
This family-owned BYOB spot combines a bustling deli counter with an elegant sit-down dining room, serving comforting Italian-American classics for over 20 years. Domenic and Lucia's personal touch shines through from their acclaimed subs and pasta fagioli to refined dinner entrees.
Must-Try Dishes:
Yale Special Sandwich, Chicken Parmigiana Sandwich, Pasta Fagioli
What makes it special: Family-run deli and restaurant with 20+ years of neighborhood loyalty and BYOB policy