3. Chicago Midway International Airport
Opened: 1923 (first established), 1931 (first terminal opened)
Annual passengers: 22.2 million
Delayed flights: 17% arrivals, 21% departures
And yet... anyone who bitches about O'Hare has never flown through Chicago Midway. Yes, O'Hare is the ninth circle of hell, but it is also the busiest airport in the world, so while we're not really willing to give it a "pass," per se, there is some rational acceptance that goes with the O'Hare experience. But there is no excuse for Midway. The airport is tiny, comparatively speaking, and it serves approximately 8,700 times the number of flyers that it was designed to, and this is never more obvious than when you are in the mile-long cattle corral that is meant to serve as the security line. The last two times I flew out of Midway, the delays in security were so bad that people who were stuck in line and about to miss their flights had to go one by one through the line asking other flyers to let them pass. I was one of those people the first time, but managed to not miss my flight only because it was delayed (natch). The second time was so bad I just gave up and resigned myself to missing my flight, looking on with sympathy at other desperate souls (PLURAL) trying to beg their way through the line. Security lines are never a picnic, but I have yet to experience anything else on the level of Midway's daily disaster.
2. Newark Liberty International Airport
Opened: 1928 (first established), 1953 (first new terminal replaced original)
Annual passengers: 37.5 million
Delayed flights: 25% arrivals, 25% departures
And then there’s Newark, which has the enviable distinction of being the worst airport in the country according to math, taking into account factors like the number of cancelled flights, the average delay time, and the number of minutes it takes to taxi to the gate. Newark has long lines for check-in, long lines for security, long lines for club lounges, long lines on the tarmac waiting for take off. Plus it's ugly and dirty and is also at least an hour from NYC, so in the event of a long delay, a trip to the city isn't necessarily feasible. Also expect broken trains and escalators, spotty and not-free Wi-Fi, zero power outlets, and crappy limited seating (with armrests that don’t move, so good luck if you get stranded overnight and don't want to pay for an offsite hotel in, ugh, New Jersey).