Nonstop route
Chicago to San Diego nonstop
Yes — Southwest flies MDW to SAN nonstop year-round — about 3× daily.
MDWChicago
✈
SANSan Diego
3× daily23.3 flights a week
Year-round23.3/wk Jun vs 15.1/wk Jan
$175–$275typical one-way · median $200
1,728miles nonstop
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Fares are what people actually paid: half of the 1,885 tickets in the US DOT fare survey for this route sold between $175 and $275 one way, median $200. 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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