So this is what I'm packing and isn't necessarily what you should pack since I have never actually been to Chicago in Fall/Autumn before. However, based on some research and weather.com predictions (and maybe some luck), I should be good with these picks. I pray for sunny days and comfortable nights with as little rain as possible. I figured an umbrella is still handy for both sunny and rainy days, especially as we plan to do a lot of site-seeing outdoors.
I think layering might also be key with cardigans or lighter jackets but I'm not 100% sure what to expect especially for nighttime temperatures/winds considering it's called The Windy City. Any and all advice welcomed especially from Chi locals or those familiar with the weather around this time of year!
I can't wait to see you tomorrow, Chicago and I'll catch you next week friends!