Take the elevator to the 96th floor of the John Hancock Center and order a beverage while looking out over the city from some 1000ft up in the sky. It’s particularly gape-worthy at night. Ladies: don't miss the bathroom view.
The lounge and restaurant have a separate elevator from the Hancock's observatory; look for signs that say 'Signature 95th/96th.' Children aren't allowed in the lounge after 7pm.