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Uh, think I figured it out.  DFW Rotation 7424, Dec 22, 2002.  
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His Christmas trip in 2002 had him in SDF Christmas eve.  I remember it well because he rented a car there and drove through a massive blizzard to get to his parents house in IND.  It was one of those trips that leaves you stranded for a day, so he essentially had Christmas 'off' (SDF overnight) and left SDF early on the 26th.  His captain that trip lived in CVG, and he rented a car and drove home.
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 Supposed to be a MCI and double SAN layover, ended up MCI/ORD/ONT!  Got back Christmas day.  Seem to remember having to buy a heavy winter jacket in the SLC airport thanks to reroute sending me to ORD in the dead of winter vice sunny SAN!
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Bah, heavy winter coat for ORD?  I used to do MQT trips in the winter wearing a skirt & heels (no boots)!
*singing to the tune of 'We Wish You a Merry Christmas'* 
We wish you a merry re-route, we wish you a merry re-route.........
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If this is the one, did he mention Dick's Last Resort near the Navy Pier in Chicago?  Gahhhh.....
If it is, and he does, my previous disclaimer applies! 
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Don't think it was him, but sounds like you had a good time 
  He had lots of DFW trips while he was back on RSV last year.