Direct flights from Oakland to Chicago OAK → MDW

Southwest Airlines operates nonstop flights from Oakland (OAK) to Chicago (MDW). The nonstop flight takes around ~3h 42m, covering 1,840 miles (2,961 km). Updated 11 June 2026.

Southwest Airlines WN

Departure Schedule next 7 days

More nonstops from Oakland

OAK → ABQ Albuquerque OAK → AUS Austin OAK → BOI Boise OAK → BUR Burbank OAK → BJX Silao OAK → BLI Bellingham OAK → HNL Honolulu, Oahu 3 airlines OAK → LIH Lihue, Kauai 3 airlines

Frequently asked questions

Is there a direct flight from Oakland to Chicago?

Yes, Southwest Airlines operates nonstop flights from Oakland (OAK) to Chicago (MDW).

Which airlines fly direct from Oakland to Chicago?

Southwest Airlines operates nonstop flights from Oakland to Chicago.

How long is the flight from Oakland to Chicago?

The nonstop flight from Oakland to Chicago takes ~3h 42m (approximately 2961 km).

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