Best Outdoor Dining Restaurants in Wicker Park & West Town (60622)
6 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
Homestead on the Roof is a garden-topped restaurant above Roots Handmade Pizza, pairing a seasonal, globally influenced menu with an intimate rooftop setting. Diners come for pork belly, seafood, and tacos built around produce and herbs grown in the rooftop garden. It leans more like a date-night or small-group dinner spot than a casual drinks-only patio.
Must-Try Dishes:
Pork Belly, Scallop, Duck Rice
What makes it special: A tucked-away rooftop garden restaurant focused on seasonal, chef-driven plates.
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.
8.2
Vibes:
Outdoor Dining Oasis
Brewery & Beer Garden Republic
Happy Hour Hotspots
Group Dining Gatherings
Forbidden Root is a botanical-themed brewpub where house beers pair with chef-driven plates on a sidewalk patio and in a polished dining room. Guests treat it as a West Town standby for tasting through floral, herb-driven beers alongside burgers, share plates, and seasonal brunch.
Must-Try Dishes:
Savory Pancake with kimchi and cheese curds, Brunch Burger, Chorizo Poutine
What makes it special: House-brewed botanical beers matched with thoughtful pub fare on a busy patio.
8.1
Beatnik West Town is a bohemian, globally inspired restaurant with lush decor, strong cocktails, and sidewalk and patio seating along Chicago Avenue. It’s a go-to for long, shared-plate dinners where the atmosphere leans as much party as restaurant.
Must-Try Dishes:
Crispy artichokes, Hummus with house flatbread, Lamb kebab skewers
What makes it special: Maximalist, plant-filled space pairing Mediterranean small plates with serious cocktails.
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.