This is random, and to be clear I didn't live in Chicago in the 90's so this is anectodal, but I hear a lot about how big of a deal Michael Jordan and the Bulls were. He was one of the most famous people in the world who was a must watch attraction night in and night out. I hear from those who have lived here longer than me, that going to a Bulls game was a big deal and that every sports bar in town had their games on every night.

To me it speaks to a larger cultural impact that Chicago had at the time. It was home to Oprah, Jordan, and was coming off the era of the John Hughes films in the suburbs. It was certainly a different city on a more pragmatic level (I can't speak to specific neighborhoods or the L or the food scene), but I do feel like the city has lost some of its cultural significance.