Flights from Chicago (MDW) to Oakland (OAK)

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

Show route on mapAll flights from MDWAll flights to OAK

Direct flights

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

  • Southwest Airlines · 270 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 · MDW → OAK
  • 1 stop(s) · 6h 53m · MDW → OAK
  • 1 stop(s) · 6h 54m · MDW → OAK
  • 1 stop(s) · 6h 54m · MDW → OAK
  • 1 stop(s) · 6h 59m · MDW → OAK
  • 1 stop(s) · 6h 3m · MDW → OAK
  • 1 stop(s) · 6h 3m · MDW → OAK
  • 1 stop(s) · 6h 14m · MDW → OAK
  • 1 stop(s) · 6h 21m · MDW → OAK
  • 1 stop(s) · 6h 23m · MDW → OAK
  • 1 stop(s) · 6h 23m · MDW → OAK
  • 1 stop(s) · 6h 23m · MDW → OAK

Timetable coverage

Published flight numbers: WN2779, WN3461, WN1413

Flight number: WN 2779

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

  • MDW 10:15 → OAK 12:40

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