honestly, I have Major issues using my credit card for anything. hell, I am going on an inclusive trip to SF this week, and I am still hesitant to use my card even for hotel ( which I know will be covered).
So the choice is up to you.
If I had to say one way or another, I would choose to hit chicago and then sit out the rest... however, the fan boy in me says hit everything and the rest will work itself out. make your choice, but know that only you can make your financial decision for you.