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

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United States US
All scheduled flights from OAK to MDW. You can fly from Oakland to Chicago non-stop on every weekday and the flight takes about 4 hours. Flights with stops take between 5 to 11 hours depending on your flight and connection airport.
OAK-MDW
- 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 OAK and MDW with Southwest Airlines is the fastest option. The flight takes about 4 hours and 10 minutes.

Yes. You can also arrive at Chicago Ohare International, ORD if you fly from Oakland (OAK).

MDW is the IATA airport code for Chicago Midway International Airport, Midway International Airport, Illinois.

The transfer from MDW is 28 minutes by car to Downtown Chicago.

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

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

It all depends on what dates you plan on flying. But the approximate round-trip price for one passenger with Southwest is $421.