Best Group Dining Restaurants in Near South Side
9 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
The Staley
A modern, chef-led sports bar where carefully cooked wings and pizzas meet cocktail-focused happy hours.
Notable Picks
#1
The Staley
8.4
The Staley is a chef-driven sports bar from former Bear Israel Idonije and chef Stephen Gillanders, turning out crisp Buffalo wings, pizzas, and game-day snacks in a polished South Loop room. It functions as a higher-end happy hour spot where cocktails and wings feel more upgraded than typical bar fare.
Must-Try Dishes:
Buffalo Wings, Neapolitan-Style Pizza, Poutine
What Makes it Special: A modern, chef-led sports bar where carefully cooked wings and pizzas meet cocktail-focused happy hours.
#2
Brûlée
8.3
Vibes:
Brunch Bliss Spots
Trendy Table Hotspots
Birthday & Celebration Central
Group Dining Gatherings
Brulee is a modern, Black-owned brunch spot on South Michigan where shrimp and grits, chicken and waffles, and a signature brûléed French toast lean indulgent. Reservations and a 90-minute seating window keep the lively, high-volume dining room moving through weekend breakfast service.
Must-Try Dishes:
Shrimp and Grits, Brulee French Toast, Lobster Tail with Sweet Potato Waffle
What Makes it Special: A high-energy South Michigan brunch room focused on soulful, plated breakfasts.
#3
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.
8.2
La Cantina Grill is a South Loop Mexican staple near McCormick Place, combining a full bar, broad menu, and a sizable vegan offering. It’s where locals, convention-goers, and families converge for fajitas, enchiladas, and margaritas before events or casual dinners.
Must-Try Dishes:
Traditional Enchiladas, Shrimp Fajitas, Mayan Tamales
What Makes it Special: High-volume South Loop cantina with a full bar, broad vegan-friendly menu, and flexible seating near Soldier Field and McCormick Place.
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.
7.8
Opened in 2025, Southern Chicago is a Southern American steakhouse in the South Loop where tomahawks, dry-aged strips, and wagyu burgers share the stage with braised collards and baked mac. The room leans polished and celebratory, pulling pre- and post-game crowds from nearby arenas and convention traffic.
Must-Try Dishes:
Tomahawk Steak 32oz, Dry Aged New York Strip, Lobster Mac & Cheese
What Makes it Special: A design-forward Southern steakhouse marrying tomahawks with classic sides.
#7
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.
7.6
Since 2013, Chicago Oyster House has been a Prairie District corner spot for oysters, sushi, and prime steaks a short walk from McCormick Place. Locals and convention-goers alike use it as a compact bar-and-dining-room stop where shellfish towers and big-ticket cuts anchor dinner before or after events.
Must-Try Dishes:
Prime Filet Mignon Steak, Prime New York Strip Steak, Fresh Oysters on the Half Shell
What Makes it Special: Neighborhood oyster bar that also grills serious prime steaks.
#9
Sakana Sushi
7.5
Vibes:
Cheap Eats Budget Brilliance
Group Dining Gatherings
Quick Bites Champions
Comfort Food Classics
A Wabash corridor Japanese spot that’s geared toward value-driven sushi ordering with a menu that spans rolls, nigiri, and warm comfort items. Best used as an efficient group pick when you want lots of variety at a friendly price point, not as a precision omakase-style experience.
Must-Try Dishes:
Salmon avocado roll, Spicy tuna roll, Tonkotsu ramen
What Makes it Special: A value-tilted sushi menu that supports big, variety-heavy orders.