My first time in chi town during a college trip for a school's convention. Everyone else flew but I took the greyhound bus because the school only gave me $400 for the trip.

It was during the fall and windy as heck. Had my first chicago style pizza that you have to eat with a fork.
Took a stroll to see what downtown has to offer. Mc dees is loaded with kaydoo workers then it hits me, Michael jordon and oprah, both kaydoos live somewhere near here so I was in the kaydoo infested part of downtown.
Took their subway system to the convention center. First time riding the subway too. Just like the movies, everyone looking important and what a morning rush.
Years later, 2nd trip was a clubbing trip. Drove from MN to milwaukee and from milwaukee to chicago which was rather a short distance drive. A highway stretch had like 5 different tolls with no workers there to collect your change. You had to throw your loose change into a tin can looking contraption to proceed. Got there for hotel check in and perfect timing for the clubs. We went looking for asian people and just followed them like a stalker. They took us to a korean underground club. Not much memory to what happened after that. Either I KO or alcohol is a blur. What I did remembered is waking up the next day, sunday and we went to a local asian car dealership and planning to buy a used car.
Few years later was spending overlay at the greyhound bus depot in chicago. Took a route from Narleans down south to MN route.
Haven't been back since.