Places to go for a night out?!

Perfect first date or girls night out is dinner and a movie. On a date, you don't have to talk a lot, you can just gauge each other's reactions to the movie or what/how they eat to learn more about the person and small talk your way through it. It is not original, but it is classic for a reason....for a first date. As you get to know each other more, that is not the only thing you should be doing to have fun together.

You can also do a live event...ball game, concert, dancing, lecture, casino, exhibit, symphony, comedy club...

Midweek might include some sort of lessons or classes...cooking, dancing, art and craft, photography, sports or exercise class.

Just like the other guy said, but by Chicago there is this very nice theater that's restaurant/movie theater. So that can be an alternative instead of doing them separately.

Somewhere that they can just sit and people watch. Maybe grab dinner or coffee. It's always better to be able to talk when you're getting to know someone. So I always rule out movies until later.