Calgary to Chicago - $400 roundtrip after tax
Chicago doesn't go on sale all that often, it usually hovers around $550-$700 roundtrip after tax.
US Airways just lowered their October/early November flights to $400 roundtrip after tax. They're via Phoenix though, so it's not exactly the most direct route.
October 27 to Nov 3 for example.
Look for the flights that are $141 each way before tax on http://www.USAirways.com
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