Long time reader, first time poster...decided it was time to start contributing.
SEA-ORD-DCA today on the way back from a work trip. 12/30 on the upgrade list for SEA-ORD, but cleared ORD-DCA (which is now delayed ~40 minutes and leaves later this afternoon) segment a little over 24 hours out. Flight is at an odd time back to DC, so I'm sure that helped. I have cleared DCA-ORD once before a couple of months ago.
FWIW, I made Platinum with a challenge earlier this year, will requalify for next year next week, and have already booked enough flights to get me to EXP later this year--my 12-month rolling EQD is probably at the upper end of Platinum.