Best Happy Hour Wings Restaurants in Magnificent Mile & Streeterville (60611)
5 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
Jake Melnick's Corner Tap
A longtime Magnificent Mile sports bar where an award-winning wing program is the main draw.
Notable Picks
8.5
A few steps off Michigan Avenue, Jake Melnick's runs as a wings-first sports bar where smoked, fried, and sauced wings headline happy hour alongside long tap lists. Locals and visitors lean on it for game-day crowds, big portions, and reliably crispy wings from afternoon into late night.
Must-Try Dishes:
Firecracker Wings, Poncho Wings, XXX Wings
What makes it special: A longtime Magnificent Mile sports bar where an award-winning wing program is the main draw.
8.3
Timothy O'Toole's is a long-running Streeterville basement pub known for award-winning wings, 70-plus TVs, and one of the denser beer lists near Navy Pier. After-work regulars and sports fans use happy hour for discounted drinks before settling into baskets of bone-in and boneless wings through the night.
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.
8.2
Vibes:
Happy Hour Hotspots
Trendy Table Hotspots
Business Lunch Power Players
Group Dining Gatherings
On the Gold Coast side of 900 North Michigan, Doc B’s runs a polished American restaurant and bar where oven-roasted wings share space with salads, burgers, and cocktails. Happy hour draws a mix of shoppers, hotel guests, and office groups who pair drinks with chimichurri-dressed wings at the bar.
Must-Try Dishes:
Oven Roasted Chicken Wings, Oven Roasted Teriyaki Chicken Wings, Housemade Guacamole with Sweet Potato Chips
What makes it special: A busy Gold Coast restaurant-bar where crisp, high-heat roasted wings fit alongside cocktails and composed plates.
8.0
Perched above Rush Street, Upstairs at The Gwen is a rooftop lounge where skyline views, cocktails, and happy hour bites—including sauced wings—drive the experience more than volume eating. It’s the move when you want wings and drinks wrapped in fire pits, city views, and hotel-bar polish.
Must-Try Dishes:
Curried Carrot Deviled Eggs, Spanakopita with Honey, Apricot-Cranberry Scones
What makes it special: Art Deco-inspired rooftop terrace with cocktails, snacks, and fire pits.
Worthy Picks
7.7
Monarch & Lion is a Streeterville British pub with Indian influences where daily happy hour brings $2 chicken wings alongside pies, curries, and cocktails. It’s quieter than the big sports bars, making it a good call when you want flavored wings in a sit-down setting with proper glassware and table service.
Must-Try Dishes:
Happy Hour Chicken Wings (Charcoal Smoked Buffalo), Lamb Keema Pie, Chili Cheese Naan
What makes it special: A design-forward British pub where daily happy hour wings come in global flavors.