Flights from Oakland (OAK) to Chicago (MDW)

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

Show route on mapAll flights from OAKAll flights to MDW

Direct flights

1 direct option(s) across 1 airline(s) · 2,961 km route distance.

  • Southwest Airlines · 253 min · 2961 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 53m · OAK → MDW
  • 1 stop(s) · 6h 53m · OAK → MDW
  • 1 stop(s) · 6h 54m · OAK → MDW
  • 1 stop(s) · 6h 54m · OAK → MDW
  • 1 stop(s) · 6h 59m · OAK → MDW
  • 1 stop(s) · 6h 3m · OAK → MDW
  • 1 stop(s) · 6h 3m · OAK → MDW
  • 1 stop(s) · 6h 14m · OAK → MDW
  • 1 stop(s) · 6h 21m · OAK → MDW
  • 1 stop(s) · 6h 23m · OAK → MDW
  • 1 stop(s) · 6h 23m · OAK → MDW
  • 1 stop(s) · 6h 23m · OAK → MDW

Timetable coverage

Published flight numbers: WN2211, WN2744, WN2761, WN3059

Flight number: WN 2211

Operating days: 7

  • OAK 05:05 → MDW 11:10

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 OAK →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.
Back to full map