Best Trendy Restaurants in Near South Side
8 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Oliver’s
A vintage-glam South Loop dining room where a meticulously built cheeseburger sits alongside Michelin-noticed cooking and cocktails.
Notable Picks
#1
Oliver’s
8.6
Set in the former Acadia space, Oliver's is a 1930s Los Angeles–inspired supper club where a chef-driven cheeseburger shares the menu with roast chicken, seafood, and cocktails. Recent Michelin Guide attention and national coverage highlight a burger built on excellent beef, buttered sesame bun, and nuanced sauce.
Must-Try Dishes:
Oliver's Cheeseburger, Roast Chicken with pan jus, Truffle Gnocchi
What Makes it Special: A vintage-glam South Loop dining room where a meticulously built cheeseburger sits alongside Michelin-noticed cooking and cocktails.
#2
Casa Tulum
8.4
Casa Tulum brings a Tulum-inspired, seafood-leaning Mexican menu to the South Loop with beachy decor, cocktails, and a more polished dining-room feel. It’s used for date nights and small groups looking for quesabirrias, ceviches, and composed plates rather than basic combo platters.
Must-Try Dishes:
Quesabirrias, Torta Ahogada, Shrimp Ceviche
What Makes it Special: Design-forward Mexican seafood spot where quesabirrias, ceviches, and cocktails are served in a Tulum-inspired room.
#3
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.
#4
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.
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
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.
7.9
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.
#8
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.