Southwest disappointment

We are on vacation and our late night flight to Oregon got delayed by almost 3 hours, we didn’t get to our destination until 3 a.m. This much of a delay has never happened to us on southwest before , I’m blaming covid. The airline blamed weather.
 
Are there certain daily flight times that seem to be cancelled the most recently? Or are the times all throughout the day? I’m just wondering if more evening flight are being cancelled or if the cancelled flights are happening in the morning?
 
I had two non-stop flights switched to one or two stops in last year. We have non stop reservations to Orlando in November - expecting SW to pull same fast one again.
 
We had a Friday evening Southwest flight last week from Denver to MCO. When we checked our luggage they said 10 minute delay. No problem. After getting my family of 6 through security and off the train to the gate we get a text that the flight was cancelled due to weather (not sure at which location). We were rebooked for a flight the next day, had to fly to Salt Lake City first, then Orlando. Couldn't get our bags back, boarding group went from A24 to C58. Our 3.5 hour flight turned into 8 hours on the plane. All very frustrating but I know it could have been worse. Really hoping our return flight goes as scheduled.
 

Milwaukee to Orlando is 19 hours each way driving. I just can't fathom a situation where that's preferable to spending like, two or three hours max in a connecting airport. I think your solution is knee-jerk – just my opinion.

Well, it isn't just the 2-3 hours in the connecting airport. Even with a direct flight DFW to MCO we get the same amount of vacation time driving as we do flying and leaving/returning home at the same time.

We live in the exurbs, so airport shuttles don't come to our house. We arranged for a local Uber driver to take us. We'd never used her before, so we had to leave enough extra time in the schedule to get there with Plan B. So, leave the house Friday at noon. We'd gone carry-on only and our stuff was spread out into 20 of those bins because they kept saying that each had too much stuff in each. So, one bin might have my kindle and a phone cord. Huge stress. The flight was at 4pm. We sat on the plane for a bit. Then we arrive, get to the rental car place. There are discussions there because they don't have the class of car that we reserved and they want to charge us more. Then we hike to the car, load our stuff and drive to the hotel. We checked in sometime between midnight and 1 am, and crash in the beds. So 12 hours from door-to-door.

DD had desperately wanted to fly before, but after that she said "Never again". It made me sad to see how different her flight was compared to mine at about the same age. Note this was American, so not bargain basement.

Next trip we drove. We left at around the same time. Friday around noon. We stop often at gas stations we have a favorite restaurant in MS if we are hungry as we drive by. We arrive in Orlando around 6am. DH and I swap out driving and sleep when we aren't, so we even arrive rested.
 















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