Best Late Night Restaurants in Magnificent Mile & Streeterville (60611)
6 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
Gibsons Bar & Steakhouse
Classic Chicago steakhouse institution where oversized prime steaks meet big-night energy.
Notable Picks
8.9
Vibes:
Birthday & Celebration Central
Business Lunch Power Players
Group Dining Gatherings
Trendy Table Hotspots
Gibsons is the archetypal Gold Coast steakhouse, where hulking USDA Prime cuts, stiff cocktails, and a perpetual buzz draw locals, tourists, and celebrities into the wood-paneled dining room. Portions are oversized, the energy leans party-like, and decades of repeat business have turned it into a default choice for both celebrations and business dinners.
Must-Try Dishes:
W.R.'s Chicago Cut bone-in ribeye, Chicago-style bone-in filet mignon, Carrot cake slice
What makes it special: Classic Chicago steakhouse institution where oversized prime steaks meet big-night energy.
8.7
Vibes:
Luxury Dining Elite
Date Night Magic
Business Lunch Power Players
Birthday & Celebration Central
RL Restaurant, attached to the Ralph Lauren flagship on the Mag Mile, delivers classic American club fare—steaks, lobster rolls, and composed salads—in a wood-paneled dining room that feels timelessly tailored. It functions as both a power-lunch address and a special-occasion destination, with service calibrated for lingering meals rather than quick turns. Pricing is steep, but the experience leans heavily into atmosphere and ritual.
Must-Try Dishes:
Lobster Roll, RL Burger, Chopped Vegetable Salad
What makes it special: Clubby Ralph Lauren decor pairs with polished, old-school American cooking.
8.5
Open since 1992, Timothy O'Toole's is a basement-level Streeterville pub with dozens of TVs, a long tap list, and wings that regularly appear on local best-of lists. Bone-in and boneless wings come with sauces like traditional buffalo, Irish Ghost, and garlic parmesan, making it a dependable choice for late games and casual meetups.
Must-Try Dishes:
Buffalo Wings, Irish Ghost Wings, Garlic Parmesan Wings
What makes it special: A long-running Streeterville sports pub where big-screen games and customizable wing baskets define the experience.
#4
Terrace 16
8.3
On the 16th floor of Trump International Hotel, Terrace 16 pairs skyline and river views with contemporary American plates, cocktails, and a patio that runs late into the evening. Diners come as much for the panorama and table-side s'mores as for the mains, making it a popular choice for late-night drinks and dessert.
Must-Try Dishes:
Lobster Arrabbiata, Ora King Salmon, Terrace Burger
What makes it special: A riverfront terrace sixteen floors up where steak, seafood, and classic brunch dishes come with close-up Chicago River and skyline views.
#5
Labriola
8.0
Vibes:
Family Friendly Favorites
Group Dining Gatherings
Business Lunch Power Players
Pet Friendly Paradise
Award-winning deep dish and thin-crust pizzas anchor this spacious Magnificent Mile Italian eatery, blending European tradition with American passion. Dog-friendly patio and versatile menu make it a neighborhood anchor.
Must-Try Dishes:
Award-Winning Deep Dish, Margherita Thin Crust, Pan Pizza
What makes it special: Award-winning pizza in a vast space right off the Magnificent Mile
Worthy Picks
Chicago’s first Australian all-day café in Streeterville runs from 6 a.m. to 11 p.m., shifting from brekkie plates and flat whites to burgers, parmas, and wine at night. It’s a design-forward, hotel-adjacent space that works for casual late dinners when you want something less touristy than Michigan Avenue’s big rooms.
Must-Try Dishes:
Chapel Street Breakfast, Glenmore Burger, Melbourne Hot Jam Doughnuts
What makes it special: An Aussie-inspired all-day cafe where thoughtful brunch plates and coffee meet a stylish, high-ceilinged room.