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All scheduled flights from Chicago to Oakland (MDW-OAK)

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United States US
All scheduled flights from MDW to OAK. You can fly from Chicago to Oakland non-stop on every weekday and the flight takes about 4 hours and 44 minutes. Flights with stops take between 6 to 11 hours depending on your flight and connection airport.
MDW-OAK
- Flight has a long layover time at the stop-airport and will affect your flight time.
- Change of terminals at the layover airport. This can go quickly or take time depending on the airport.
- Flight is partially or completely overnight (Red-eye flight).
- Airline or one of the airlines in the flight path is a low-cost carrier. Some travelers wants to avoid low-cost airlines.
- This is codeshare flight. A codeshare flight is an agreement between airlines to sell seats on each others flights. Click on the flight to see the actual flight operator.

Flying non-stop between MDW and OAK with Southwest Airlines is the fastest option. The flight takes about 4 hours and 35 minutes.

OAK is the IATA airport code for Metropolitan Oakland International Airport, Oakland, California.

OAK has 44 flight routes and 280 arriving and departing passenger flights every day.

The transfer from OAK is 25 minutes by car to Downtown San Francisco.

Airlines that offer direct flights from Chicago (MDW) to Oakland (OAK) is Southwest Airlines.

The Boeing 737MAX 8 Passenger with Southwest Airlines has 174 seats and the Boeing 737-800 (winglets) Passenger/BBJ2 with Southwest Airlines has 159 seats.

It all depends on what dates you plan on flying. But the approximate round-trip price for one passenger with Southwest is $381.