Direct flights from Oakland to Chicago
All flights from OAK to MDW non-stop. There are direct flights from Metropolitan Oakland International (OAK), California, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 13 weekly departures are currently scheduled on this route. Departure times range from 05:05 to 23:55 depending on the schedule period. The flight distance is 1850 miles (2977 km). Flight time ranges from 4 hours to 4 hours and 5 minutes.
Oakland
, USA
Flight schedule from Oakland to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-07-13
Oakland to Chicago scheduled departures
Select a date to see every published non-stop departure between OAK and MDW.
OAK - MDW route facts
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Distance1850 miles (2977 km)
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Flight time4 hours to 4 hours and 5 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Departure terminalsTerminal 2
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AircraftBoeing 737-800 (winglets) Passenger/BBJ2, Boeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)
