1531 N. Damen Ave. 773-235-4039
The most notoriously popular patio in the ’hood, this taco-and-whiskey bar’s outdoor seating is a hot commodity, with tables often filling in the early afternoon on sunny days.
1059 N. Wolcott Ave. 773-486-1512
A bar that looks like any no-frills dive gives way to a room filled with pingpong tables and a seriously spacious patio out back. It’s technically just south of Wicker Park proper, but the outdoor imbibing space is among the best in the area, if not the whole city.
1846 W. Division St. 312-878-1212
This sleek restaurant is known for its sustainable and organic focus, but the unique patio, with loungey couches and shady umbrellas for long afternoons of people-watching, is just as much of a draw.
1616 N. Damen Ave. 773-772-7100
The eclectic menu at this eatery offers a little bit of everything, from coconut-curry quesadillas to salmon with avocado salsa. It’s all best enjoyed on the side patio, which is partially covered for rainy days.
2146 W. Division St. 773-772-7700
Division Street is known for shady seating on its extra-wide sidewalks, but the real al fresco action at this Italian eatery and wine bar is the fenced-in backyard patio, lined with greenery and shaded with rose red umbrellas.