Airlines with flights from Oklahoma City to Chicago
There are two airlines with scheduled flights between OKC and MDW. Southwest is the only airline with non-stop flights from Will Rogers World to Midway International Airport and the flight time is 1 hour and 55 minutes.
There are two airlines with scheduled flights between OKC and MDW. Southwest is the only airline with non-stop flights from Will Rogers World to Midway International Airport and the flight time is 1 hour and 55 minutes. Choose airline
Direct
Non-stop
1h 55min
Via Dallas
3h 55min
Via Minneapolis
4h 36min
Via Nashville
4h 40min
NEW
Starts 11/09
Via Detroit
4h 31min
NEW
Starts 13/09
Via Detroit
5h 25min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 1 hour and 55 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
14 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Direct
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3052
----
05:45
05:45
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----
05:00
----
WN3121
05:00
----
----
----
----
----
----
WN1773
----
----
----
05:15
05:15
----
----
WN360
----
----
----
----
----
----
05:25
WN4807
----
----
----
----
----
11:30
----
WN4865
----
----
----
----
----
----
14:45
WN3232
----
15:20
15:20
15:30
15:30
----
----
WN3123
15:50
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-22
Via Dallas with Southwest Airlines
-
Total flight time: 3h 55m - 6h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
14 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Via DAL
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3109
WN4386
WN4386
05:45
----
----
----
----
----
----
WN3042
WN586
WN586
----
----
----
----
----
06:05
----
WN7
WN694
WN694
----
06:50
06:50
----
----
----
----
WN4303
WN1225
WN1225
----
----
----
15:55
15:55
----
----
WN1303
WN107
WN107
16:40
----
----
----
----
----
----
WN4303
WN1312
WN1312
----
----
----
----
----
----
17:35
The timetable & schedule information was updated at 2026-04-22
Via Minneapolis with Delta Air Lines
-
Total flight time: 4h 36m - 6h 30m.
-
Sky Team Alliance
-
21 flights per week
OKC
Via MSP
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL3844
DL4820
DL4820
07:40
07:40
07:40
07:40
07:40
07:40
07:40
DL5142
DL4714
DL4714
11:48
11:48
11:48
11:48
11:48
11:48
11:48
The timetable & schedule information was updated at 2026-04-22
Via Nashville with Southwest Airlines
-
Total flight time: 4h 40m - 7h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
36 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Via BNA
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3040
WN1827
WN1827
----
----
----
----
----
07:00
----
WN3107
WN507
WN507
07:35
----
----
----
----
----
----
WN3040
WN573
WN573
----
07:35
07:35
----
----
----
----
WN146
WN930
WN930
----
----
----
----
----
----
07:55
WN1291
WN576
WN576
----
----
----
14:10
14:10
----
----
WN726
WN576
WN576
----
14:20
14:20
----
----
----
----
WN2241
WN577
WN577
----
----
----
----
----
----
16:10
WN3108
WN4286
WN4286
16:15
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-22
Via Detroit with Delta Air Lines
-
Total flight time: 4h 31m - 4h 31m.
-
Sky Team Alliance
OKC
Via DTW
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-22
