Stay the F away from O'hare, it's a seriously terrible airport. Depending on where I'm going, if Minneapolis-St.Paul makes sense for my route, I find that a very efficient airport and also a decent place to kill some time. The Mall of America is only one train stop away.
Whatever the airline lets you schedule should be fine. I pulled a half hour layover in Frankfurt on the way from Zurich to Calgary and it was fine. Walked straight on to the second flight.
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