Best Group Dining Gatherings Italian Restaurants in Near South Side
3 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Flo & Santos
A pizza-first South Loop room where Italian comfort overlaps with pierogi classics.
Notable Picks
#1
Flo & Santos
8.3
A loud, high-energy South Loop tavern where thin-crust pizza is the default and Polish comfort dishes make it easy to feed a mixed-age table. It works best when you keep the order tight: one pizza for the table plus one shared plate, then decide if anyone still needs a chicken parm or entrée.
Must-Try Dishes:
Thin-crust pizza, Pierogi, Chicken parmigiana
What makes it special: A pizza-first South Loop room where Italian comfort overlaps with pierogi classics.
Worthy Picks
7.9
This South Loop outpost of the Chicago-based Pizano's group serves deep-dish and thin-crust pies, pastas, and salads a short walk from McCormick Place and Wintrust Arena. It’s a go-to for groups and travelers who want recognizable Chicago-style pizza with full bar service near the convention center.
Must-Try Dishes:
Rudy's Special Deep-Dish Pizza, Thin-Crust Sausage and Pepperoni, House Salad
What makes it special: Convention-area pizzeria offering deep-dish and thin-crust with full bar and TVs.
#3
Cafe Bionda
7.8
Cafe Bionda is a South Loop Italian restaurant and bar known for old-school recipes, martinis, and a lively dining room a short ride from McCormick Place. Guests lean on hearty pastas, chicken dishes, and tiramisu before or after conventions, games, and downtown events.
Must-Try Dishes:
Joe's Mama's Meatball Salad, Short Rib Ravioli, Tiramisu
What makes it special: South Loop martini-and-red-sauce spot blending classic Italian with bar energy.