What things should I know before going to Chicago?

You need to know that there's lots of fun things to enjoy but some irritations. Bike crime for one, parking and traffic jams for another. If you know this, you can plan around it. Public transport is good and you can get to other cities easily.

There's a good choice of music scene, or museums if that's your preference. It's crowded, let's be frank. So if you go for a lakeside bike ride, so is everyone else. The lake looks like an ocean - until it freezes over. Remember, summer there is short and winter is very long, wet and windy.