Can anybody humor me and tell me what to pack for a short weekend in Chicago? The plan includes two nice dinners and a matinee of Hamilton. Weather is projected to be in the 60's day, 50's night. It's a girls' weekend type of event. I am swamped by work and can't even think what to pack. Also, it has been in the 80's and 90 percent humidity all month where I live, which probably clouds my thinking further.

Some random finds of things from my closet are below. Feel free to ignore the finds and opine freely. I suppose I need two plane outfits, one dinner outfit, one play/dinner outfit, and one bopping-around-in-the-morning-before-play-and-dinner-outfit.

P.S. This is a type of thing I am really bad at.

Weather forecast:

ETA: added some more finds