I was at Athleta with a client on Friday, and they have EXTREMELY good puffers at the moment! That's my suggestion

You've gotten great advice here. I would just add: make sure you have *wool* socks to wear in those boots. You can also add toe warmers if needed for Chicago - if you place a hand warmer on the top of your foot, it warms the blood heading to the toes. Fleece/sherling insoles can also elevate a non-insulated boot in a major way. And perhaps you could order a puffer when you're stateside - as others have mentioned, Lands End, Eddie Bauer, and Athleta are all good options.

I was in Uniqlo yesterday and they had a nice thick puffer: https://www.uniqlo.com/us/en/p.....5&

Also this is what I wear when I visit Portland and it's great (note it runs small so size up): https://www.amazon.com/gp/prod.....1&

Thanks all! I have a good collection of wool socks.

I will actually be packing two or three weeks early for the trip due to our summer vacation. And of course aside from underwear it is an entirely different collection of clothing due to it being mid summer here. Another option is borrowing my husbands Uniqlo puffer which fits me well. It’s not a packable one but it is nice.

I hesitate to buy a longer puffer online. The hip fit is hard on me and often to fit my hips I size up and then it can be too large on top. I will either buy out of season here, borrow from family, or go shopping in person in Portland on day one of the trip.