What's the difference between doing something "on the fly" and "wing it"? If I'm not mistaken, both are informal but is there a difference in meaning?

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They both mean to do something without planning ahead. But I think they can be used in slightly different contexts. In my opinion, “on the fly” often has the meaning of making a unexpected change while in the middle of something. For example, if you’ve participating in a debate that you prepared for, but you’re asked a question that you didn’t anticipate, you’d have to come up with a response “on the fly.”

To “wing it” often means that you didn’t prepare at all, even for something you knew about (and probably should have prepared for). For example, if you’re participating in a debate and you didn’t bother preparing at all, you’ll just make up responses as you go along, you’ve decided to “wing it.”