Best Happy Hour Restaurants in Wicker Park & West Town (60622)
7 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
Big Star - Wicker Park
A high-energy taco-and-bourbon patio that defined modern Wicker Park hangs.
Notable Picks
8.5
Big Star turns Wicker Park’s Damen and North corner into a taco-and-bourbon patio party, with al pastor and pork belly tacos backed by a deep whiskey list. Huge review volume and constant crowds make it one of the city’s most visible modern taquerias, especially for outdoor season and late nights. It’s less about quiet meals and more about tacos, pitchers, and people-watching in a high-energy setting.
Must-Try Dishes:
Al Pastor Taco, Pork Belly Taco, Beer-Battered Fish Taco
What makes it special: A high-energy taco-and-bourbon patio that defined modern Wicker Park hangs.
8.4
Queen Mary Tavern is a nautically themed cocktail bar in Ukrainian Village known for classic martinis, $1 oyster happy hour, and a tight bar-snack menu. It feels like an old-world ship’s bar translated to Division Street, with low lighting, polished service, and a serious spirits list.
Must-Try Dishes:
Martini with olive or twist, Oysters on happy hour, Clam chowder with bread
What makes it special: Cocktail-first bar with a famous martini program and oyster happy hour.
8.2
Vibes:
Birthday & Celebration Central
Outdoor Dining Oasis
Trendy Table Hotspots
Instagram Worthy Wonders
Paradise Park is a trailer-park-themed pizzeria and bar where tavern-style pies, frozen drinks, and loaded apps fuel loud nights on a sprawling patio. Groups use it for birthday parties and day-drinking sessions when they want playful pizza more than serious, quiet dining.
Must-Try Dishes:
Special K Pizza, Buffalo Chicken Pizza, Party Boi Pizza
What makes it special: Party-forward patio destination for loaded pizzas, drinks, and kitschy décor.
#4
Elia
8.1
Vibes:
Birthday & Celebration Central
Date Night Magic
Girls Night Out Approved
Group Dining Gatherings
Elia is a Mediterranean restaurant in West Town where happy hour often revolves around Greek wines, mezze, and a sidewalk-facing bar. It’s more polished than the average special–drinks spot, drawing dates and small groups who want saganaki, grilled seafood, and a proper cocktail list.
Must-Try Dishes:
All-you-can-eat mezze and grill spread, Lamb chops, Baklava dessert
What makes it special: Modern, music-forward Mediterranean room built for lingering celebrations.
8.0
Vibes:
Business Lunch Power Players
Comfort Food Classics
Solo Dining Sanctuaries
Trendy Table Hotspots
Dove's Luncheonette channels a retro counter-and-booth setup into a daytime spot for Tex-Mex and Southern-inflected plates, ideal for creative-industry lunches. It’s comfortable enough for one-on-ones at the bar or a booth, with food that feels substantial without knocking you out for the afternoon.
Must-Try Dishes:
Chicken-fried chicken, Shrimp and grits, Smoked brisket tacos
What makes it special: Retro diner energy with chef-driven Tex-Mex and Southern plates.
8.0
Vibes:
Outdoor Dining Oasis
Brewery & Beer Garden Republic
Brunch Bliss Spots
Family Friendly Favorites
The Perch Kitchen & Tap is a brewpub on Division Street with a sculpture garden-style patio, Finch beers, and wood-fired cooking. It works as a flexible outdoor spot for brunch, burgers, and rotisserie meats when you want something a step up from a bar patio.
Must-Try Dishes:
Wood-grilled steak, Rotisserie chicken, Rotisserie cauliflower
What makes it special: Brewpub with a sculpture garden patio and live-fire menu.
8.0
Rootstock is a Humboldt Park wine and beer bar where the kitchen’s seasonal plates and burger draw as much attention as the bottle list. Happy hour here looks like discounted pours, comfortable bar seats, and small plates that feel more like dinner than snacks.
Must-Try Dishes:
Dry-aged Slagel Farms burger, Hand-cut fries with garlic aioli, Cheese and charcuterie selection
What makes it special: Cozy wine bar where a serious burger and seasonal plates anchor happy hour.