Best Trendy Italian Restaurants in Loop
3 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Gino's East - South Loop
A family-built deep-dish experience where the long bake time is part of the ritual.
Notable Picks
8.4
Vibes:
Family Friendly Favorites
Group Dining Gatherings
Comfort Food Classics
Trendy Table Hotspots
A classic Chicago deep-dish stop in Printer’s Row that’s built for families who want a sit-down pizza night with a little spectacle. The move is to commit to one deep dish (it takes time) and add one appetizer so the table stays happy while the pie bakes.
Must-Try Dishes:
Deep dish pizza (sausage or spinach Margherita), Homemade mozzarella sticks, Thin crust veggie pizza
What Makes it Special: A family-built deep-dish experience where the long bake time is part of the ritual.
#2
Acanto
8.3
A Michigan Avenue dining room that leans modern-rustic with a serious pasta-and-wine backbone. The best meals here are built around one composed pasta (rigatoni or cacio e pepe) plus a crisp starter, then finished with a classic dessert so the pacing stays clean.
Must-Try Dishes:
Rigatoni, Arancini, Tiramisu
What Makes it Special: A refined Loop Italian that pairs pasta craft with a strong wine-bar sensibility.
Worthy Picks
7.8
A hotel-adjacent Loop trattoria built for all-day dining—equally useful for a weekday lunch as it is for a simple dinner. Stick to one pasta plus one classic red-sauce plate or flatbread so the meal feels cohesive rather than scattered.
Must-Try Dishes:
Chicken parmesan, Penne arrabbiata, Eggs benedict florentine
What Makes it Special: An all-day Loop Italian inside the Kimpton Gray, designed for easy drop-ins.