Best Rooftop Restaurants in Wicker Park & West Town (60622)
4 hand-picked restaurants, critic-reviewed and ranked
Last Updated: January 2026
Our Top Pick
Taxim
Rooftop-friendly modern Greek spot emphasizing regional dishes and meze.
Notable Picks
#1
Taxim
8.5
Taxim is a Wicker Park Greek restaurant known for shareable meze, rustic mains, and a rooftop space used in warmer months. Guests pair dishes like duck gyro and souvlakia with Greek wines while lingering over long dinners. The setting skews lively and slightly upscale, making it a go-to for dates and group celebrations rather than quick bites.
Must-Try Dishes:
Wood-grilled octopus, Braised lamb shank, House mezze platter
What makes it special: Rooftop-friendly modern Greek spot emphasizing regional dishes and meze.
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.
Worthy Picks
7.8
Perched atop Hyatt Place Chicago / Wicker Park, Kennedy Rooftop serves American share plates, burgers, and cocktails with unobstructed skyline views. People book it for sunset drinks, igloo experiences in colder months, and casual bites before or after going out in Wicker Park. The food is approachable bar fare, with the atmosphere and views doing much of the heavy lifting.
Must-Try Dishes:
Prairie Land Wings, Rooftop Double Stack Burger, Mango Mojito
What makes it special: Skyline-focused rooftop with igloos, cocktails, and elevated bar bites.