Okay, so I'm massively kicking myself. Yesterday evening, I found two dream MR itins: a $436 a/i SFO-FRA on UA/LH, and SFO-FRA-DCA-ORD-SFO for $593 (!) on UA. I went out to a show with a friend, came back at 10pm ("It's not midnight yet, I'm sure the fares are still there"), and... well, you know the story, the fares had increased by 50-100%. :-(

Now I'm back trying to do a MR for 10K miles on Star Alliance AND trying to fit two separate trips to visit friends in D.C. and Chicago. Here's my problem, though: I'm using ITA and I can't figure out how to construct the ideal itin whereby I fly far enough east to get 5K miles RT each time, yet stop over in Chicago or D.C.

I tried doing a multi-segment: SFO;SJC - phl;pit;mco;fll;tpa;pbi;nyc;bos - CHI - SFO;SJC, but it kept routing me into, say, PHL and out (an hour later) of PIT. That's no good!

Any strategy ideas here? I'm free to travel pretty much anytime on these two flights between now and Dec 20. Thanks! :-)