I went out to Los Angeles a couple of weeks ago, and because it was significantly cheaper I flew through Chicago, rather than direct. Not ideal, but liveable on the way out (although I was really annoyed when they gate-checked my bag from Boston straight through to LA - if I was going to check a bag, I would have packed completely differently!).
I was really not looking forward to the trip home, though - I was scheduled on a red-eye flight to Chicago followed by an early morning flight to Boston. I was tired and ready to go home by about 5PM and my flight didn't leave until 11:30. So I decided to go to the airport a little early and see what my other options were. The little check-in computer was uninterested in letting me change my flights BUT it also asked me if I would be willing to give up my seat on the Chicago flight, which was overbooked (as near as I could tell, another Chicago flight had been cancelled).
"Hmm," I said to myself, "this seems like an opportunity - the airline doesn't want me to go to Chicago, and I don't want to go to Chicago either!" After a half-hour of wandering around the terminal and checking on the little check-in computers to see if there were any other flights available, I found the customer service line. Which I then waited in for 45 minutes.
Easily half the movement of the line was people getting frustrated and walking away (yikes!), but I persevered. I was wearing comfortable shoes and I had podcasts to listen to. But finally, I got up the front of the line, just as boarding was starting for the direct LAX-BOS flight!
I explained the situation to the woman at the desk, and she said, "If it'll make one of the Chicago people happy, no problem. But I have to type like the wind!" She gave me a boarding pass and said she didn't know if it was a good seat or anything but I figured I didn't have a particularly good seat on the Chicago flight, and this way I didn't have to go to Chicago. And when I boarded the plane, my seat was a perfectly nice window seat and, get this, the seat next to me was empty! I think it was the only empty seat on the plane!
I got home hours earlier than I expected, I didn't have to get off the plane in Chicago at 5AM (5AM Chicago time, so 3AM LA time), and I got to spread out and take as much sleeping room as I wanted for the whole flight. It was awesome. All it took was 45 minutes of waiting in line, and let's face it, I was already in the terminal and it's not like I had anything better to do with my time. I felt triumphant. Travel Win!