Direct flights from Chicago to Oakland MDW → OAK
Southwest Airlines operates nonstop flights from Chicago (MDW) to Oakland (OAK). The nonstop flight takes around ~3h 42m, covering 1,840 miles (2,961 km). Updated 11 June 2026.
MDW
→
OAK
Round trip
1 adult
Economy
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Southwest Airlines
WN
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Frequently asked questions
Is there a direct flight from Chicago to Oakland?
Yes, Southwest Airlines operates nonstop flights from Chicago (MDW) to Oakland (OAK).
Which airlines fly direct from Chicago to Oakland?
Southwest Airlines operates nonstop flights from Chicago to Oakland.
How long is the flight from Chicago to Oakland?
The nonstop flight from Chicago to Oakland takes ~3h 42m (approximately 2961 km).