......may be through Chicago. Some serious headwinds aloft made this trip a little different. A friend of mine was on this flight. (flightaware.com) More...
My Airline uses flight plans called LIDO which calculate the cheapest route based on winds and other factors. Many time "Direct" is not the fastest or cheapest. The example you gave is ann extreme example of this.
I worked that flight, thought the route was odd but the winds were 120 knots by VHP and only 30-40 knots at JOT. Winds have been strong all week almost 200kts at FL360
I stumbled onto this one Fri morning the 4th, when checking out the ABQ action. On closer look at all west bound traffic, across TX, NM and other states, they were really bucking a strong headwind, while east bound traffic has been whistling along, over 500kts. I flew HP ATL-PHX in Dec 2002 and it took us over 5hrs to complete the trip due to headwinds. All the way across TX it was like riding on buckboard roads.
Yeah that's what I noticed. When I saw the flight plan, I had to look to see why. It seems like a lot more than 244 miles out of the way too! Direct 1663 - As flown 1907