It's a big city, that is for sure.
It just doesn't have the same cachet/rep as New York.
I've been once, briefly. I've also been to NY, for a week.
I'd go back to NYC. There are quite a few things I didn't get to do/see first time round, and there are quite a few that I can't wait to do/see again.
There are things in Chicago I do want to see--Wrigley Field, Sears Tower, ride the L--etc.
But given my limited travel budget, it would be NY again ahead of Chicago.
That said, my last trip was Hong Kong and Hanoi. The trip was to Hong Kong, and I went to Hanoi for a couple days because I wanted to see another city in East Asia, one that wasn't identical to Hong Kong, and one that was within my flight budget.
I knew very little about Hanoi, and I loved every minute of my visit. One surprise after another, all of them good.
In short? Try to do both.
