I fly out of Midway in Chicago when going to Toronto because I like Porter Airlines and the fact that they fly into Island Airport in downtown Toronto as opposed to Pearson, which is pretty far out. I feel going out of Midway instead of O'Hare is a small price to pay. Here is the exception: flying out on an early flight on a Monday morning during Spring Break. Today it was by far the worst I had ever seen. The security line went, literally, out into the parking deck and curved back inside. The escalators going down to the security line were shut down. It was a nightmare, and I have no doubt that many people missed their flights. For people on non-refundable spring break flights with their family in tow, that's so bad. It's not like it's great for anyone. Since I almost always get to the airport early, I actually made my flight, but barely. So if you are going out of Midway on any Monday morning, go early. If it's during Spring Break, you might want to camp out the night before.