Generally when booking a trip, I try to find the least painful flights with no connections or at least the easiest connections. I never check bags if possible and try to fly at the least congested times. For my theoretical summer 2008 trip, I'm trying to find flights to Europe that don't go through Heathrow, so I can avoid that kerfuffle. But right now I'm dealing with something different: the mileage run:
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Husband is/was a frequent flyer; he was flying to CA back and forth every week until April, now he's working more locally. As of today, he has
89,137 elite-qualifying miles, 10,866 miles shy of the all-important Executive Platinum status. Our upcoming trip to Nicaragua will add another 4,240 miles, leaving 6,626 to go. Why is this so important? Well, aside from being automatically upgraded on domestic flights when available, getting bonus miles on all flights, and generally being treated like a human being: there are the eVIPs. These are systemwide upgrades you can use to fly first class at coach prices. These precious things have allowed us to fly to Chile and Ireland in first class for a few hundred bucks a ticket and get miles at the same time. There's also the skip the line element: at Heathrow for one, we were able to totally skip a line like this. But beyond that, it's just a matter of pride. H will be damned if he flew 90,000 miles just to barely miss out on the EXP goodness.
We kept hoping he'd be staffed on another project that would require flying by year's end, but now that it's November, we are starting to sweat those last 6,626 miles. I've been spending more and more time each day trying to figure out the most horrific flights that will bring him closest to the 100k goal without costing us a fortune. Unless tickets are very cheap, this will probably be a solo trip, so I am taking great joy in finding the most painful flights for maximum miles. Some contenders, all over Thanksgiving, may I add:
La Guardia to Boston to LA to Reno: 3175 miles, 14 hours including layovers
Return via LAX to Newark: a piddly 2,841 but pretty good for $579
LGA to Chicago O'Hare to Dallas to Calgary: 3,052 miles, 13 hours including layovers
Return through Dallas: 2,890, still nearly 700 miles short
So the key, I think, is to choose cities as far across the country as possible that don't offer many direct connections. American Airlines in their infinite wisdom, makes it impossible to get to Reno without flying to California. And Calgary is north of Seattle, why wouldn't you fly to the southwest first?! Sucks for anyone who might need to get there in a convenient way, but great for us. I'm going to have to spend much more time studing the boards at Flyertalk.com and searching American's website if we are going to be serious about getting these miles, but I'm enjoying the journey. Which H certainly won't.
The Notorious M.E.G. blogs 
FASCINATING. You must keep us updated on the progress. Now that you mention it, i remember T's friend Danny drove an hour north to Memphis to fly to Biloxi and back the weekend in-between christmas and new year's, just to get to the next level of miles. And this was after they'd just returned from a trip to Japan!