Yeah depends on what you want to do. The two really famous churches are The St. Joseph Oratory, and the Notre Dame Basilica. The oratory is nicer.
Since it's gonna be cold if you're there in winter, definitely check out the underground (it's really a set of building basements downtown that are interconnected with tunnels, and filled with stores). According to wikipedia, it's the largest such thing in the world.
Night life is pretty damn amazing.
I think somewhere around the old port, there are ice sculptures, which are kinda nice.
I usually only go back (I grew up in Montreal) in the summer time, since that's when all the awesome festivals are around, and there's just more to do.
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