Direct flights from Oakland to Chicago OAK → MDW
Southwest Airlines flies nonstop from Oakland (OAK) to Chicago (MDW), daily. The flight takes about 4h 18m and covers 1,840 miles (2,961 km). Arrivals run on time 78.2% at OAK and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 28 July 2026.
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Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 13 flights per week (~2 per day) · Updated 33d ago
Southwest 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 ~4h 18m (approximately 2961 km).
How often do direct flights operate from Oakland to Chicago?
Nonstop flights from Oakland to Chicago operate daily — 13 flights per week (~2 per day).
What is the on-time performance for flights from Oakland to Chicago?
Arrivals run on time 78.2% at OAK and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
What days of the week are there direct flights from Oakland to Chicago?
Direct flights from Oakland to Chicago operate every day of the week.
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