Kennedy Rooftop

The Kennedy Rooftop delivers that rare Chicago trifecta: skyline views that actually live up to the hype, cocktails worth their downtown price tag, and enough space that you won't spend your evening in an elbow-to-elbow shuffle. Perched atop the Wicker Park hotel, this spot offers a panoramic feast of downtown architecture that somehow makes even your $16 Old Fashioned taste better.

The craft beer selection impresses even the most discerning hop heads, while the full food menu means you can transition seamlessly from afternoon drinks to dinner under the stars. Yes, it attracts its share of tourists snapping skyline selfies, but the heated sections make it a viable option even when Chicago decides summer is officially canceled for the day.

Come for happy hour to avoid the weekend crowds, or bring a date when you're ready to impress without explicitly saying "I'm trying to impress you." Just be warned: your neighborhood dive will seem disappointingly horizontal after an evening here.