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

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

Show route on mapAll flights from MDWAll flights to SJU

Direct flights

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

  • Southwest Airlines · 280 min · 3314 km

Explore these airlines on this city pair

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Southwest Airlines route map →

Stopover options

  • 1 stop(s) · 6h 20m · MDW → SJU
  • 1 stop(s) · 7h 35m · MDW → SJU
  • 1 stop(s) · 7h 37m · MDW → SJU
  • 1 stop(s) · 7h 39m · MDW → SJU
  • 1 stop(s) · 7h 39m · MDW → SJU
  • 1 stop(s) · 7h 40m · MDW → SJU
  • 1 stop(s) · 7h 40m · MDW → SJU
  • 1 stop(s) · 7h 40m · MDW → SJU
  • 1 stop(s) · 7h 43m · MDW → SJU
  • 1 stop(s) · 7h 43m · MDW → SJU
  • 1 stop(s) · 7h 43m · MDW → SJU
  • 1 stop(s) · 7h 44m · MDW → SJU

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 MDW →Explore all arrivals to SJU →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 SJU when return timing is important.
  • Use Guides for alliance and hub strategy playbooks.
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