Nonstop route
San Jose to Chicago nonstop
Yes — Southwest flies SJC to MDW nonstop in the summer season only — about daily.
SJCSan Jose
✈
MDWChicago
daily14 flights a week
Summer only14/wk Jun vs 3.2/wk Jan
$200–$325typical one-way · median $225
1,838miles nonstop
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Fares are what people actually paid: half of the 843 tickets in the US DOT fare survey for this route sold between $200 and $325 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.
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