Chicago is a lovely town for culinary and beverage---Blackbird, Avec, etc. Plus Joey Buono's Italian Beef sangwidges (full dip).
Missouri is well worth seeing but a caution: it can be appalling as well as beautiful...in a wine sense, I mean. It has long been a vinous area, surprisingly, with some very well developed vineyards and long track records. Vinifera and American and hybrids; they're all there.
Missouri poses problems primarily because of the heat/humidity and extreme bugginess afflicting the area, so sometimes good wines are a struggle.
There's some damned good wine. There's also an inordinate amount of what, for wine geeks, is absolute trash. Both exquisite and ham-fisted wine making exist. Nagging tendency toward the masses--those darned masses---that aren't wine drinkers and so looooooove sweet and sticky wines.
So you'll get varied experiences. One winery I visited had not one single potable wine out of the entire line of ten that I tasted. And some of it was so egregiously flawed, in a variety of ways, as to be a textbook example of everything that could go wrong with a winery.
On the other hand, have had some sublime dessert and fortified-style wines (quasi-ports mostly) from Missouri, and have even doled out gold medals in competitions for them. For still reds Norton/Cynthiana wines are good. Seyval and Vidal have at times shown well.