Cerise Rooftop

Cerise Rooftop delivers that rare Chicago experience where the skyline feels close enough to touch. The wraparound views create an electric atmosphere as sunset paints the glass towers gold and cocktail glasses clink against the backdrop of Lake Michigan.

Their cocktail program shines brightest—try the house specialty with bourbon and local honey that somehow tastes like summer in the Midwest. The full menu offers solid companions to your drinks, with the truffle fries emerging as the crowd favorite.

Yes, you'll spot tourists snapping skyline selfies, but the space is large enough that you won't feel like you're drinking in someone's Instagram story. The live music (usually jazz or acoustic sets) hits the sweet spot—present enough to create ambiance without drowning conversation.

Fair warning: on perfect weather days, everyone in Chicago has the same idea. Book ahead or risk the disappointment of watching the sunset from street level like a common pedestrian.