A: Midway is smaller and perhaps a bit easier to navigate. I haven't noticed that either is significantly better than the other when it comes to security screening lines.
Both airports have trains that terminate there and take you right downtown for $1.75. The Orange Line from Midway lets you off at Wabash and Adams, almost right in front of the meeting location. The Blue Line from O'Hare takes perhaps 10 minutes longer and lets you off a few blocks over. In general, Chicago has a good public transportation system and it's often the preferred mode of travel even for folks who can afford to travel by cab, car or shuttle.
Shuttles and cabs are about the same cost from either place, cabs perhaps $30 or $35 and shuttles about half that much. The traffic is probably easier from Midway. O'Hare traffic can be jammed up for four hours, in both directions, in morning and evening.
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