Flights from San Juan (SJU) to Chicago (MDW)

Route intelligence for SJU → MDW: direct flights, stopover options, and timetable coverage in one place.

Show route on mapAll flights from SJUAll flights to MDW

Direct flights

1 direct option(s) across 1 airline(s) · 3,314 km route distance.

  • Southwest Airlines · 290 min · 3314 km

Explore these airlines on this city pair

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Southwest Airlines route map →

Stopover options

  • 1 stop(s) · 6h 0m · SJU → MDW
  • 1 stop(s) · 6h 10m · SJU → MDW
  • 1 stop(s) · 6h 14m · SJU → MDW
  • 1 stop(s) · 6h 15m · SJU → MDW
  • 1 stop(s) · 6h 16m · SJU → MDW
  • 1 stop(s) · 6h 16m · SJU → MDW
  • 1 stop(s) · 6h 17m · SJU → MDW
  • 1 stop(s) · 6h 17m · SJU → MDW
  • 1 stop(s) · 6h 17m · SJU → MDW
  • 1 stop(s) · 6h 17m · SJU → MDW
  • 1 stop(s) · 7h 37m · SJU → MDW
  • 1 stop(s) · 7h 47m · SJU → MDW

Timetable coverage

Flight numbers are not published in the current source dataset.

Plan this city pair

Compare nearby alternatives and airline networks to decide whether a direct trip, one-stop connection, or reverse search gives you better options.

Explore all departures from SJU →Explore all arrivals to MDW →Compare airline network coverage →Browse airports by country →

Route planning checklist

  • Compare direct duration with one-stop total duration before committing to a fare.
  • Check inbound alternatives on flights to MDW when return timing is important.
  • Use Guides for alliance and hub strategy playbooks.
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