How's Chicago in the wintertime? I absolutely loved it in Chicago when I was here earlier this month for a birthday trip and would love to come back.

Is the cold much worse than NYC? Do you guys get a ton of snow? Please let me know before I make my decision. Thanks!

and a decent amount of snow.  This year we already have snow which is unusual but I am not sure if that means we will have a cold hard winter or not TBH.  It tends to be really unreliable in that way

But is is cold enough that gentleman spend more time in and less time golfing making the winters financially rewarding.  
Good luck but truthfully I would wait until early spring.
Alyssa

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Chicago is always beautiful, but you can't enjoy the beauty if you're freezing for fashion lol. never know if you're going to encounter bitter cold one day, and semi-cold the next.  

Look hot when you get there, and when you start to freeze, pull out the packable down. They go down I think to -7 degrees to keep you warm.

I think this year El Nino is supposed to keep us a little warmer. (Insert the squiggly line over the "n" for all of the grammar nazis.)

Hoping for a beautiful Jan-March business wise for tax season - lol. As of now, pre-bookings have all the bills paid plus some, but I could use more to make sure I can pay the piper. lol

i would love to keep you warm..

It could 30 degrees or a windchill of 30 below. It just depends on travel dates.  Chicago weather is unpredictable.

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but i want some..