Best Happy Hour Restaurants in Magnificent Mile & Streeterville (60611)
7 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
The Purple Pig
High-volume Mediterranean small plates spotlighting pork and Spanish-leaning tapas.
Notable Picks
8.8
Opened in 2009 by chef Jimmy Bannos Jr., The Purple Pig is a high-volume Mediterranean small-plates restaurant on the Magnificent Mile where pork, offal, and vegetable dishes pull from Italian, Greek, and Spanish flavors. A Bib Gourmand pedigree, tens of thousands of reviews across platforms, and an always-busy dining room make it one of downtown Chicago’s most proven small-plates destinations.
Must-Try Dishes:
Milk Braised Berkshire Pork Shoulder, Charred Cauliflower, Pork Belly
What makes it special: High-volume Mediterranean small plates spotlighting pork and Spanish-leaning tapas.
8.6
Vibes:
Brunch Bliss Spots
Quick Bites Champions
Business Lunch Power Players
Instagram Worthy Wonders
Beatrix - Streeterville is an all-day neighborhood restaurant and coffeehouse where bakery cases, vegetable-leaning plates, and comfort classics draw hospital staff, hotel guests, and locals from early breakfast through late dinner. The menu leans on recognizable American dishes with health-conscious twists, plus standout desserts and a serious coffee program. It has become a default choice in Streeterville for reliable, slightly polished everyday dining.
Must-Try Dishes:
Hot Honey Fried Chicken Sandwich, Prime Cheeseburger, Mushroom & Quinoa Burger
What makes it special: An all-day cafe fusing comfort food, lighter plates, and serious coffee.
8.6
On the seventh floor of the Four Seasons, Adorn uses its Michelin Guide recognition and skyline views to turn pre-dinner drinks into a full-blown happy hour occasion. Guests treat the bar and lounge as a cocktail-first destination, pairing inventive drinks with polished small plates before downtown dinners or events.
Must-Try Dishes:
Wagyu beef cheeks, Charred octopus, Coconut-crusted snapper
What makes it special: A Four Seasons dining room where chef-driven plates meet cocktails, skyline views, and live music.
#4
Marisol
8.5
Marisol, set inside the Museum of Contemporary Art, serves vegetable-forward New American plates, a standout burger, and seasonal proteins in a dining room that mirrors the museum’s clean, contemporary aesthetic. It pulls a mix of museum-goers and neighborhood regulars who treat it as a calm, design-minded alternative to louder Streeterville spots. The cooking is more careful and market-driven than the casual setting might suggest.
Must-Try Dishes:
House Smashburger, Seasonal Roasted Chicken, Farmers’ Market Vegetable Plates
What makes it special: Museum-adjacent, market-driven cooking in a calm, contemporary dining room.
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.
8.0
Operating since 1974, Pippin’s Tavern now pairs its neighborhood-pub DNA with a modern American menu and weekday happy hour. It’s a relaxed option just off the Mag Mile where office groups lean on beers, cocktails, and bar food instead of a high-concept scene.
Must-Try Dishes:
Pippin's Smash Burger, Char Broiled Burger, $1.50 Oyster Happy Hour
What makes it special: A nearly 50-year-old pub that now layers legit gastropub food onto classic happy hour structure.
Worthy Picks
#7
101 Bar
7.8
The 101 Bar & Grill anchors a multi-level bar and rooftop complex at Rush and Erie, pairing Mediterranean-inspired dishes with burgers, salads, and a strong cocktail focus. Guests come as much for the covered patio and skyline rooftop as for the food, making it a social, view-driven way to work Mediterranean flavors into a night out.
Must-Try Dishes:
Hummus with Warm Pita, Grilled Salmon Entrée, Chicken Sliders
What makes it special: A Mag Mile–adjacent bar and grill where rooftop views, cocktails, and Mediterranean-leaning plates share the spotlight.