For romance, 360 Chicago (Hancock) is hit or miss.
The lake-and-shoreline view here is arguably better framed than Willis, and the 94th-floor CloudBar lets you nurse a cocktail right at the glass instead of filing through. The catch: the old Signature Lounge two floors up — long the free-view-for-a-drink hack — closed in 2023 and is being rebuilt into a multi-floor observation expansion (targeted ~2027), so that workaround is gone, and the deck itself is smaller and can feel cramped at sunset.