O’Hare (ORD).

When? Every time I’ve flown through it.

Longest? 20 hours… I think… My brain has tried to blank that period of time out to save my sanity.

Now I avoid flying through ORD at absolute all costs. DTW, DFW, DEN, hell even ATL are better to fly through. 3 years ago my family flew to Kauai. On the way out we connected in DEN, which went great. On the way back we had to make two stops, first at LAX, the second at ORD. We made it through LAX with no issues. Got to ORD and had a 10 hour delay. The only reason why I didn’t rent a car and drive home was due to being awake for 30 hours at that point (I don’t sleep on planes). Also, the plane was always “just one more hour away”.