Direct flights from Chicago to Oakland

MDW - OAK route map All flights from MDW to OAK non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Metropolitan Oakland International (OAK), California, USA every day of the week with Southwest Airlines. The flight distance is 1850 miles and the trip usually takes about 4 hours and 35 minutes.

MDW
Chicago Midway
USAChicago , USA
OAK
Metropolitan Oakland International
USAOakland , USA
MDW
Chicago Midway
USAChicago , USA
Metropolitan Oakland
USAOakland , USA
OAK
Flight time is 4 hours and 35 minutes
CHANGE DIRECTION

Airlines with non-stop routes:

Southwest Airlines

S
M
T
W
T
F
S
Low-cost airline
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1-3 flights per day
1-3 flights per day
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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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
Mon
Apr 14
Tue
Apr 15
Wed
Apr 16
Thu
Apr 17
Fri
Apr 18
Sat
Apr 19
Sun
Apr 20
WN2937
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16:55
16:55
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16:55
12:50
WN261
21:10
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21:10
21:10
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The timetable & schedule information was updated at 2025-03-15

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Chicago to Oakland flight departures

Select a date to see all scheduled flight departures between MDW to OAK.

Monday
Mon
Apr 14
1 flights(1)
Tuesday
Tue
Apr 15
1 flights(1)
Wednesday
Wed
Apr 16
1 flights(1)
Thursday
Thu
Apr 17
1 flights(1)
Friday
Fri
Apr 18
1 flights(1)
Saturday
Sat
Apr 19
1 flights(1)
Sunday
Sun
Apr 20
1 flights(1)
Time
Airline
Flight
21:10
Southwest Airlines Southwest Airlines
WN261
16:55
Southwest Airlines Southwest Airlines
WN2937
16:55
Southwest Airlines Southwest Airlines
WN2937
21:10
Southwest Airlines Southwest Airlines
WN261
21:10
Southwest Airlines Southwest Airlines
WN261
16:55
Southwest Airlines Southwest Airlines
WN2937
12:50
Southwest Airlines Southwest Airlines
WN2937
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MDW-OAK flight route
Chicago, MDW to Oakland, OAK flight path. The distance is 1850 miles or 2977 km.
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Chicago - Oakland direct flight map
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MDW - OAK information

  • Distance
    1850 miles (2977 km)
  • Flight time
    4 hours and 35 minutes
  • Airlines
    Southwest Southwest
  • Alliances
    One World
    Sky Team
    Star Alliance
  • Classes
    Economy
    Business
    First Class
  • Southwest Aircraft
    Boeing 737 Passenger
  • Arrival Terminal
    Terminal 2 (Southwest)
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Yes. You can fly direct to Oakland (OAK) every day with Southwest Airlines.

The flight time is 4 hours and 35 minutes. The distance is 1850 miles or 2977 kilometers.

There are approximately 6 flights every week with departures between 07:30 and 21:30.

No, there are no direct flights from Chicago to Oakland with Star Alliance.

No, there are no direct flights from Chicago to Oakland with oneworld.

No, there are no direct flights from Chicago to Oakland with SkyTeam.

Southwest flies this route with the Boeing 737 Passenger aircraft.

Southwest have non-stop flights to Oakland.

You can fly direct every day of the week.
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