Flights from San Jose (SJC) to Chicago (MDW)

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

Show route on mapAll flights from SJCAll flights to MDW

Direct flights

1 direct option(s) across 1 airline(s) · 2,950 km route distance.

  • Southwest Airlines · 245 min · 2950 km

Explore these airlines on this city pair

Open each airline route-map page to compare broader network depth before committing to a nonstop or one-stop strategy.

Southwest Airlines route map →

Stopover options

  • 1 stop(s) · 6h 55m · SJC → MDW
  • 1 stop(s) · 6h 5m · SJC → MDW
  • 1 stop(s) · 6h 5m · SJC → MDW
  • 1 stop(s) · 6h 5m · SJC → MDW
  • 1 stop(s) · 6h 10m · SJC → MDW
  • 1 stop(s) · 6h 10m · SJC → MDW
  • 1 stop(s) · 6h 12m · SJC → MDW
  • 1 stop(s) · 6h 12m · SJC → MDW
  • 1 stop(s) · 6h 13m · SJC → MDW
  • 1 stop(s) · 6h 13m · SJC → MDW
  • 1 stop(s) · 6h 15m · SJC → MDW
  • 1 stop(s) · 6h 17m · SJC → MDW

Timetable coverage

Flight numbers are not published in the current source dataset.

Route graph estimate

Operating days: 1, 2, 3, 4, 5, 6, 7

  • SJC 21:28 → MDW 01:40

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 SJC →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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