It’s been a few years since I lived there, but my favorite thing to do with tourists was take them up in the Hancock to the restaurant (not the observation deck) and just get a drink at the bar. Elevator ride is free that way, basically get the same view, and it comes with an expensive (but not as expensive as the observation deck) drink!

But like I said, I haven’t lived there for a few years, any current Chicagoan is welcome to contradict me if that’s changed.