One of the main problems is that due to weather airlines won't just put you on the next flight (in regards to a competitor). Airlines keep you on their planes and then everything gets backed up. I think I can be somewhat of an authority on this as I have about 370,000 miles on United, 70K on Northwest (half of those on Continental though), 45K on American, a half-dozen flights on JetBlue (they also do credits), and one each on Delta and Southwest. The problem with weather and getting rescheduled has mostly to do with when you fly, more specifically capacity. The problem with putting you on the next flight is that they can't put you on it if it is sold out. There are only a certain amount of seats on a plane, and if every one is sold out and everyone shows then they can't physically put you on that flight. If you fly around the holidays you will be lucky to get rescheduled on a flight the same day; I had a similar experience with American around Christmas in 2006 and I couldn't get rescheduled on another flight for 3.5 days; not their fault - there just were not any seats available on any flights until then. (Part of the problem was some obnoxious putz from Chicago who couldn't get it through his head that he couldn't get on the next flight, or any flight for 3 days, because they were FULL.) Weekends - Fridays and Sundays - and Mondays because of business travelers are pretty full flights too. Also if you are going to a smaller airport with fewer flights it can be a while before you can get rescheduled too (and yes, Milwaukee is a smaller airport). Also, there are very limited flights after 7PM. On the other hand, today my flight was delayed for servicing, but if a flight before it had been canceled it wouldn't have been any problem getting on this one because it was less than half full. A Tuesday in January you won't have any problem getting rescheduled. A holiday or a Friday, Sunday, or Monday is a different story. Some other traveling tips to help you understand why this happened: 1) When there are delays or cancellations, they cancel or delay the shortest flights first. That is air traffic control, not the airlines decision. That's because planes coming in from further destinations may already be in the air, and it is very difficult to turn them around and go back to the airport. So why your flight from O'Hare to Milwaukee was delayed or cancelled could have been because it was so short, and shorter flights get pushed back first. All airlines do that. 2) Airlines will hold up flights for 10-15 minutes for passengers/baggage, but no longer. If you land after the departure time, by the time you get to the gate, get off the plane, and get to your next gate will probably take more than 10 minutes, thus why they left. They can't hold up the whole system to wait 30 minutes for a couple of people; the only exception to that is international flights and they'll give you 30 minutes tops. With all airlines, if your flight lands after the scheduled departure of your next flight they will not hold it for you. Again, that is with all airlines. 3) Because of limits of how many hours crew can work, crews don't just run the same route back and forth. In order to maximize their availability they have to run different routes, thus why your crew was stuck in Pittsburgh. Again, all airlines do that. Tired pilots make mistakes; thus they can only work so many hours in a day. 4) They don't de-ice until they take off because there could be air traffic delays - they need to wait until they have clearance to take off before de-icing. If there is a delay, it can ice over again and then they might have to do it all over again and miss their window to take off. Or you can take off and crash because of ice. 5) Once they push back from the gate, no cell phone use. The pilots need to communicate with air traffic control. So if they say no cell phones, how about people actually listen to them and follow the rules? I hate to say this, but other than rude flight attendants/customer service reps, this could have happened on any airline. It's just the way the system operates. Not American's fault at all, other than a few people needing some customer sensitivity training.