Flying in the US is a consistently miserable experience. Airports which are too small for the number of flights they handle - leading to cascading gate changes and flight delays, slow & interrogative customs which you must go through even if you're getting a connecting flight straight out of the US, obvious complaints about the TSA and airlines who all (apart from Southwest in my experience) really just have no interest in making flying a pleasant or comfortable time for you.

On my most recent trip to the US I selected cities that I could get between via train to avoid the entire mess apart from arrival into the US (and made an effort to depart out of Canada).