Best Happy Hour Restaurants in Near South Side
6 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
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.
8.1
A South Loop tropical lounge that quietly accommodates plant-forward diners with real vegan bowl-and-soup options, not just side salads. The best vegetarian play is to anchor the meal with a tofu-based bowl or noodle soup, then add one snackable share plate if the table wants variety.
Must-Try Dishes:
Vegan Tofu Poke Bowl (GF), Vegan GF Garlic Tofu Noodle Soup, Togarashi Chips
What Makes it Special: A tiki-leaning room with clearly defined vegan tofu mains.
Worthy Picks
7.9
A newer South Loop steakhouse built around a lively bar-and-dining-room energy, with shareable starters, cocktails, and headline cuts like a tomahawk experience. It works best for a date that wants steak plus nightlife momentum—just time it earlier if you want lower volume and less club-like energy later.
Must-Try Dishes:
Tomahawk for Two, Short Rib Nachos, Signature Burger
What Makes it Special: A South Loop steakhouse that blends steak-forward dining with a nightlife-leaning lounge vibe.
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.