Direct flights from Chicago to Oakland
All flights from MDW to OAK non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Metropolitan Oakland International (OAK), California, USA with Southwest Airlines. 15 weekly departures are currently scheduled on this route. Departure times range from 09:35 to 23:05 depending on the schedule period. The flight distance is 1850 miles (2977 km). Flight time ranges from 4 hours and 25 minutes to 4 hours and 45 minutes.
Chicago
, USA
Flight schedule from Chicago to Oakland 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 2026-06-02
Chicago to Oakland scheduled departures
Select a date to see every published non-stop departure between MDW and OAK.
MDW - OAK route facts
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Distance1850 miles (2977 km)
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Flight time4 hours and 25 minutes to 4 hours and 45 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Arrival terminalsTerminal 2
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AircraftBoeing 737-700 Passenger (Scimitar Winglets) and Boeing 737MAX 8 Passenger
Route FAQ
Direct flights from Chicago to CA, USA
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SMF Sacramento International
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LAX Los Angeles International
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LGB Long Beach
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BUR Burbank Glendale Pasadena
From Chicago to San Diego
SAN San Diego International Airport
From Chicago to Ontario
ONT Ontario International Airport
