Nonstop route
San Juan to Chicago nonstop
Yes — United, American and Spirit fly SJU to ORD nonstop year-round — about 3× daily.
SJUSan Juan
✈
ORDChicago
3× daily21 flights a week
Year-round21/wk Jun vs 31.8/wk Jan
$150–$325typical one-way · median $225
2,072miles nonstop
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Fares are what people actually paid: half of the 3,784 tickets in the US DOT fare survey for this route sold between $150 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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