Nonstop route
Portland to Chicago nonstop
Yes — Southwest flies PWM to MDW nonstop in the summer season only — about 6× weekly.
PWMPortland
✈
MDWChicago
6× weekly6.3 flights a week
Summer only6.3/wk Jun vs 0/wk Jan
$150–$250typical one-way · median $175
895miles nonstop
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Fares are what people actually paid: half of the 69 tickets in the US DOT fare survey for this route sold between $150 and $250 one way, median $175. That survey runs a couple of quarters behind, so treat it as the shape of the route's pricing rather than today's quote.
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