Direct flights from Chicago to Oakland MDW → OAK
Southwest Airlines flies nonstop from Chicago (MDW) to Oakland (OAK), daily. The flight takes about 4h 18m and covers 1,840 miles (2,961 km). Arrivals run on time 72.8% at MDW and 78.2% at OAK — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 31 July 2026.
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Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 14 flights per week (~2 per day) · Updated 31d ago
Southwest Airlines
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 ~4h 18m (approximately 2961 km).
How often do direct flights operate from Chicago to Oakland?
Nonstop flights from Chicago to Oakland operate daily — 14 flights per week (~2 per day).
What is the on-time performance for flights from Chicago to Oakland?
Arrivals run on time 72.8% at MDW and 78.2% at OAK — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
What days of the week are there direct flights from Chicago to Oakland?
Direct flights from Chicago to Oakland operate every day of the week.
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