Where's the best place to visit in America?

Assuming you mean driving from Chicago to see some sights, there are some cool sand dunes in Western Michigan,or the Black Hills of South Dakota.Also, the Wisconsin Dells are known to be a popular destination.More obvious stuff like the Grand Canyon or Times Square NYC would be a lot of air fare and time.

I'm not sure, but I THINK we're currently deciding between San Francisco, New York, and New Orleans (maybe San Diego, too).

I'm trying to push San Francisco, so we can head to the Giant Bomb offices and visit where our relationship started, haha.

@DuskVamp: I don't know that you want to go to Yellowstone. Part of it is in "Wyoming", and Wyoming doesn't exist.