Date: 2013-04-30 02:30 pm (UTC)
A lot of the cost difference you're seeing is because Seattle to Madison is farther and less heavily travelled than New York to Madison. We generally fly through Minneapolis rather than through Chicago, with Detroit as the second choice for changing planes, because those airports are less affected by midwestern weather than Chicago.

We haven't tried the bus from Chicago to Madison, but if you fly Southwest to Midway rather than anybody else to O'Hare and are willing to risk Chicago weather-related cancellations, that could work.
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