Nonstop route
Portland to Chicago nonstop
Yes — Southwest flies PDX to MDW nonstop year-round — about daily.
PDXPortland
✈
MDWChicago
daily18.4 flights a week
Year-round18.4/wk Jun vs 7/wk Jan
$150–$300typical one-way · median $225
1,751miles nonstop
Affiliate disclosure
Ready to compare fares?
Fares are what people actually paid: half of the 521 tickets in the US DOT fare survey for this route sold between $150 and $300 one way, median $225. That survey runs a couple of quarters behind, so treat it as the shape of the route's pricing rather than today's quote.
Nonstop Scout may earn revenue from outbound flight-search links.