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Direct flights from Oakland to Chicago

Airlines Schedules

OAK - MDW route map 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 05:00 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 15 minutes.

OAK
Metropolitan Oakland
USAOakland , USA
MDW
Chicago Midway
USAChicago , USA
OAK
Metropolitan Oakland
USAOakland , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 4h 0min to 4h 15min
Updated Oct 5, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 05:00 and 23:55 • From Terminal 2
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
13 flights/week
13 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
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
Mon
Nov 2
Tue
Nov 3
Wed
Nov 4
Thu
Nov 5
Fri
Nov 6
Sat
Nov 7
Sun
Nov 8
WN1488
05:35
----
----
05:35
05:35
----
05:35
WN2871
----
06:30
06:30
----
----
----
----
WN3220
23:50
23:50
23:50
23:50
23:50
23:50
23:50

The timetable & schedule information was updated at 2026-10-05

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Oakland to Chicago scheduled departures

Select a date to see every published non-stop departure between OAK and MDW.

Tuesday
Tue
Nov 03
2 flights(2)
Wednesday
Wed
Nov 04
2 flights(2)
Thursday
Thu
Nov 05
2 flights(2)
Friday
Fri
Nov 06
2 flights(2)
Saturday
Sat
Nov 07
1 flights(1)
Sunday
Sun
Nov 08
2 flights(2)
Monday
Mon
Nov 09
2 flights(2)
Time
Airline
Flight
06:30
Southwest Airlines Southwest Airlines
WN2871
23:50
Southwest Airlines Southwest Airlines
WN3220
06:30
Southwest Airlines Southwest Airlines
WN2871
23:50
Southwest Airlines Southwest Airlines
WN3220
05:35
Southwest Airlines Southwest Airlines
WN1488
23:50
Southwest Airlines Southwest Airlines
WN3220
05:35
Southwest Airlines Southwest Airlines
WN1488
23:50
Southwest Airlines Southwest Airlines
WN3220
23:50
Southwest Airlines Southwest Airlines
WN3220
05:35
Southwest Airlines Southwest Airlines
WN1488
23:50
Southwest Airlines Southwest Airlines
WN3220
05:35
Southwest Airlines Southwest Airlines
WN1488
23:50
Southwest Airlines Southwest Airlines
WN3220
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OAK-MDW flight route
Route map from Oakland, OAK to Chicago, MDW. The distance is 1850 miles or 2977 km.
Oakland - Chicago direct flight map
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OAK - MDW route facts

  • Distance
    1850 miles (2977 km)
  • Flight time
    4 hours to 4 hours and 15 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Departure terminals
    Terminal 2
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from OAK to MDW with 13 weekly departures.

Scheduled flight time from OAK to MDW ranges from 4 hours to 4 hours and 15 minutes. The route covers 1850 miles (2977 km).

13 weekly departures are currently scheduled on this route, with published departure times ranging from 05:00 to 23:55 depending on the schedule period.

Departure terminal: Terminal 2.

Economy are currently scheduled on non-stop flights for this route.
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