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So excited for you! This looks much better in terms of the likely temperatures and should fulfill all your needs. Who knows? Maybe you will buy yourself something to wear at the party!
It's been stressful in the lead up! I would be happy to make a couple of purchases - winter clothes are always the boring part of my closet so would love to find something to add to my mix!
The trade show will be mostly people in uniform or the polo/chino look I suspect. I just need something that is smart, professional and practical. Trips a bit outside the norm do show where my wardrobe is a bit lean - I am much better set up for leisure trips.
I grew up in Ohio and have lived in Chicago for the last 40 years, and I only have one real comment. That is, bring a jacket with a hood. Rain can come out of nowhere, and I have always found it a drag to carry around an umbrella on the chance of rain. I don't think it will get to more than the upper 60s during the day, but on a lovely bright sunny day, that can feel pretty warm.