My suggestion this week for "Chicago ideas" is to to eat at Lucky's. Lucky's sandwiches all come standard with fries and a vinegar based coleslaw piled on top. The sandwich half pictured is without coleslaw as I am not a fan of coleslaw; imagine how large this sandwich would be with the coleslaw!
Lucky's is known for their "Lucky's Challenge," therefore one may wonder why I don't suggest that. Simple, the Lucky's Challenge is ridiculous. The Lucky's Challenge is to eat three of these massive sandwiches in an hour (you have to take them standard with the fries and coleslaw on top), and I can barely eat half of ONE. Personally I don't find eating until I feel as though I am going to burst to be enjoyable. That said, we went with a friend a few years ago to watch him try the challenge for his birthday, and THAT was enjoyable. Lucky's is worth the trip just for the yummy sandwiches, however, if you can talk a crazy friend (IE, not you!) into trying the challenge, the experience will be even better.