Direct flights from Chicago to Oakland

  • ~2 flights a day
  • Southwest Airlines

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When the nonstops leave

Typical weekly schedule · 14 flights per week (~2 per day) · Updated 81d ago

Morning before noon 6 a week

Arrive the same day

10:00 AMnot Sat
Afternoon noon – 6 PM 2 a week

Arrive the same day

1:20 PMSat 4:30 PMSat
Evening after 6 PM 6 a week
9:00 PMTue, Wed 9:40 PM4 days a week
Southwest Airlines Arrives Terminal 2

More nonstops from Chicago

MDW → AUS Austin MDW → BNA Nashville MDW → BWI Baltimore MDW → CLE Cleveland MDW → LGA New York MDW → MCI Kansas City MDW → MEM Memphis MDW → OMA Omaha OAK → MDW The return trip MDW All nonstops from Chicago OAK All nonstops from Oakland

Frequently asked questions

Is there a direct flight from Chicago to Oakland?

Yes. 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). Schedule data from 31 July 2026.

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 days of the week are there direct flights from Chicago to Oakland?

Direct flights from Chicago to Oakland operate every day of the week.