Second City is a great idea!
We also have tons of live clubs down town that are well worth checking out.
We have the hockey hall of fame here also, if you have any interest in hockey it's well worth the visit.
I'm sure there's more but that's all I can think of off the top of my head. But feel free to e-mail either one of us or respost and we'll tell you all you need and want to know
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And if any of you gc'ers have been to our wonderful city, let us know what you saw and enjoyed!