Nonstop route
Chicago to San Juan nonstop
Yes — Southwest flies MDW to SJU nonstop year-round — about 2× weekly.
MDWChicago
✈
SJUSan Juan
2× weekly1.9 flights a week
Year-round1.9/wk Jun vs 0.9/wk Jan
$200–$300typical one-way · median $250
2,057miles nonstop
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Fares are what people actually paid: half of the 156 tickets in the US DOT fare survey for this route sold between $200 and $300 one way, median $250. 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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