Illinois is pretty close by, and so when I wanted a city to play in, I'd plan a trip to Chicago. I've been to many conferences there since it is a hub city that is easy to fly into. And I've visited Urbana-Champagne and Evanston as part of my tour of Big Ten universities (U of Illinois and Northwestern, respectively).
The attractions of Chicago/Evanston are twofold. One, a nice big city, lots of bookstores and restaurants and shops, combined with the comfortable familiarity of Lake Michigan from my childhood. All right, Lake Michigan is on the "wrong" side of the city from the small town where I grew up, but that doesn't matter. It's still as big and beautiful and soothing to me in Illinois as it was to me in Frankfort.
I've been to Chicago by plane, by car, and by train - the latter is actually my favorite way to arrive. I fly many places - too many, really - and after a while all flights seem the same. I don't like to drive long distances unless I have company to share the driving, and even then it seems a bit like a forced march. But on a train you can see the scenery, get a coffee, read, and there is absolutely no pressure to go faster. You don't have to worry about traffic. Someone else is responsible for getting you there, so no need for maps or triptiks or GPS announcements on where to turn. It is leisurely and I like it very much.
Once in Chicago, the El is a wonderful option for getting around, although there are numerous cabs available as well. I prefer not to drive in Chicago after one memorable trip where we were stuck on the Dan Ryan Expressway through town for several hours in 90 degree heat. Cars were overheating and dying on all sides of us and it served as a caution to me for the future.
Northwestern's campus is gorgeous - the buildings are fancy and probably reflect the fact that as a private school (the only private in the Big Ten), it is pricey. The students there do enjoy a very nice campus. Good bookstores and restaurants and shops in the area make for a very pretty college town. And a commuter train gets you back into the heart of Chicago in only a little time.
Urbana-Champagne (or sometimes, Champagne-Urbana) is the home of the University of Illinois, another Big Ten school. I don't know why the town name is sometimes one, sometimes the other way. I also admit I remember very little about the university campus or nearby area. Although we did stay at the hotel/inn on campus (almost every Big Ten school has at least one), we encountered quite a bit of rain while we were there and thus the obligatory tour of campus was obscured by viewing through rain-smeared bus windows. Nice enough, I am sure, but not memorable for me.
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