Back before Wizard took it over, we looked forward to going to the Chicago Comicon each year. I'd look forward to it more than Christmas. Every year we'd save up money to go, including putting change in the bank to cover the tolls, and we'd have enough left over to have some extra spending money. We'd be making good time going up highway 65, making good time...until we got off the highway. Most times there'd be traffic and we'd have to wait in the traffic jam to make it up to the convention. We would factor that into our plans, and eventually got up to the point where we'd head up the night before so we wouldn't have to fight traffic. It was exciting seeing the comics celebrities out and about in the hotel. The first year they moved from the late Ramada O'Hare to the convention center, I was trying to get my bearings and figure out how to use the walkways to make it from the hotel to the convention center. that was nicknamed by the congoers as the habitrails. And I passed by Neil Gaiman. There it was, July, and hot inside the habitrail and he was still in his trademark black shirt and leather jacket. Even though Chicago is famous for their deep-dish pizza, ironically I was crazy about a local place's thin crust pizza that we'd get at every chance while we was up there. And on the way home we'd stop off at Godfather's Pizza (the other pizza place was closed Sundays) until Godfather's closed up there, then it was Cracker Barrel.
And eventually years of curiousity overcame us and we would venture into Chicago proper to take in the sights. There are all sorts of things to do in Chicago. We always wanted to take sightseeing tours like the kind offered by Trusted
Tours and Attractions. They offer tours across 23 cities in the US and can certainly help you with Things to do in New York City, for example with their sightseeing tours. And if you sign up for their newsletter by May 31st you can be eligible to win a iPod.