I think my most convoluted trip was an AA codeshare that had me go HOU - DFW - LAX - SFO - NRT - SYD. Happily for me my route did not take me through MIA so my bags actually arrived in SYD when I did and there was nothing obviously missing from inside. Take delight in the little things is what I always say.
So far Bench is the clear winner in the Most Improbable Itinerary category.
AA has (had?) some interesting routing algorithms — I turned down Barcelona-Madrid-Boston!!-LHR-JFK-DFW-AUS once, even though it was the cheapest route on offer. They would also routinely offer DFW-SFO as a leg on a trip from Austin to Europe.
My favorite, like your Houston to DFW, is when I’ll get a crazy stop at BWI on the way to DCA. If the pilot guns it too much on takeoff, he runs the risk of overshooting DCA, it feels like. Flight time is like 8 minutes and you never get above 5,000 feet, getting nasty looks from the Cessnas and Pipers the whole way.
I had a flight like that from IAH to Austin one night. I was coming back from somewhere, and weather in the east had screwed everything up, so I wound up sitting around IAH waiting for a plane until sometime after midnight. They finally got us a plane, got everybody on, and pushed us away. The pilot never even slowed down as he turned off the taxiway and onto the runway, and because there was no other traffic, we just took this little ballistic trajectory from one runway to the other. I think it was about 30 minutes gate-to-gate.
In February 1995 I flew from DFW to Denver Stapleton to make my quarterly meeting with the Rocky Mountain News advertising management. It was a pretty day and my return flight was in two days. What I did not realize, because my administrative staff made my reservations and I did not pay any attention, nor should I have been expected to because they knew what I wanted, was that my return flight two days later would be from the opening day of the new Denver International Airport. What a clusterfuck. First of all, a storm had rolled in overnight slowing traffic to a crawl, and secondly every media outlet was headed to the airport with a truck(s) and my cab was moving at glacial speed. I was late for my flight but my flight was late so I got back to DFW only a few hours late. If I had scheduled my flight 24 hours later I probably would have been fine. It was my first experience at opening a new, mega airport, and my last, and it was a mess. I flew in there many times since and it is a great facility.
I took that flight over a dozen times in the late 80s - early 90s. SWA hadn’t made it to Florida yet and Continental to IAH was the only non-stop option from Tampa. i wouldn’t think to have my folks drive from Galveston all the way to bumfuck Houston to get me so I hopped the Ellington Field shuttle. I don’t think that thing got over 1,500 ft off the ground.
I took it once just for the hell of it, just to say I did. I can certainly see the use case for some motorscooter driving up from Galveston, though. From where I was coming from the time savings were minimal. Pretty much six a one half a dozen or the other.
I don’t remember any additional charge for the flight, either, now that I reflect on it.
Sorry…the locals refer to DEN as DIA. I flew into the real DIA a few times before DOH opened. They didn’t have jetways, you had to take a bus from the terminal to the plane. Have had to do that in Jakarta as well.
I never missed a connection, but was once connecting in Taipei, and they were holding the connection for a few of us coming in from Jakarta. They told us before we landed, and gave us stickers to wear. There was one of those little golf cart tram things waiting at the gate and we absolutely flew through the airport at what seemed like Houston freeway speed. That was a fantastic way to get from gate to gate.
Those buses were absolutely fantastic. I could have, if we didn’t have movies and earphones and wine and snacks…watched White Chicks in Spanish, twice.