Big mountain and midwest don't go together. I'm not hating its just the truth. I have been to pretty much all the "hills" in wisconsin and michigan. Back in the day Cascade's terrain park was the best in the midwest, for many many years. Tyrol is decent, but granite peak blows away all of them as far as park is concerned. They actually have a multiple bad ass jump lines, and plenty of features.
Mt.Bohemia is the best there is. They don't make any snow, so they rely on mother nature lake effect. When the snow machine AKA the lake effect is turned on, Mt.Bohemia is a gem....However with low snow seasons bring your rock skis cause there are plenty of them. It's pretty much the only place in the midwest that you can actually ski a real mountain, and powder. Unfortunately its 7 hours from Chicago.
Chicago is great city. However the winters do really suck, because of the bitter cold and wind. The city can be very dangerous, traffic blows donkey balls, its completely flat, Illinois in general sucks, Chicago is the most corrupt city in the country, the cops blow, highest gas prices in the country, terrible taxes, terrible gun laws, high living costs, and very very high property and sales taxes.
I am doing the exact opposite of you. Around December time I will be taking a new position in Denver. I am looking forward to getting out of Chicago.