Just got back from Chicago for Spring Break (wasn't the warmest option) I tried to capture some of the city and tried to stay away from the typical tourist Michigan Ave, Sears Tower, pics.
Thanks, I have a friend who lives in the city, so I drove and saved money. I graduate this May and I am trying to save money for a trip to Europe if it all works out. When I get back, I will share a ton of pics.
Keep in mind that you can fly or take the train for about the same price as driving: $100 or less. I like to support Amtrak and see the countryside, so I'd go that route. The trip takes 8 hours, which isn't too terribly much of a penalty, particularly if you have all week. The flight to Midway takes an hour and you can hop on the orange line and be downtown in another 30 minutes or so. From the ground in KC to downtown Chicago in 2 hours. Pretty snazzy.
I prefer to park the car as often as possible and add traffic to our transportation options in the city, but that is just me.... just something to keep in mind. That, and you don't want a car in Chicago if you can help it. I have driven before and I park in the 'burbs and take rail into the city.
On a side note, Amtrak to STL is very cheap and doesn't have that much of a time penalty, saving you the trouble of driving I70. I love watching people come out of the train and down the narrow hallway to be let out into the grand hall of Union Station. It would be a shame to lose AmTrak service.
I like to take the train as well. I would have taken it if I went by myself. I went with my girlfriend and we drove her gas friendly saturn. It only cost us $40 each in gas. Plus there is this cool outlet mall on I-80 that we both like to stop at. Polo and Nike Outlets were nice stops. You're definetly right about the parking, it was a biyatch finding a spot, but we did luck out and found a street spot, and we left it there until we left. I love the fact there is a taxi at a seconds notice and the "L" was a block away.
If you're taking the train to Chicago, just make sure to take the northern route. It's a hell of a lot faster than the southern one that goes through St. Louis.