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).
-
18 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Direct
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3121
05:00
05:00
05:00
05:00
05:00
05:00
05:00
WN235
----
----
----
----
----
14:20
----
WN3123
15:50
14:55
14:55
15:50
15:50
----
15:45
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 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Via DAL
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3109
WN2744
WN2744
----
----
----
----
----
----
05:40
WN3109
WN4386
WN4386
05:45
----
----
05:45
05:45
----
----
WN3109
WN1198
WN1198
----
06:10
06:10
----
----
----
----
WN1303
WN2725
WN2725
----
----
----
----
16:40
----
----
WN1303
WN107
WN107
16:40
----
----
16:40
----
----
----
WN1372
WN1189
WN1189
----
----
----
----
----
18:10
----
WN3003
WN1359
WN1359
----
20:00
20:00
----
----
----
----
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
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL3844
DL4820
DL4820
07:15
07:15
07:15
07:15
07:15
07:15
07:15
DL5142
DL4714
DL4714
11:57
11:57
11:57
11:57
11:57
11:57
11:57
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 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
OKC
Via BNA
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3108
WN2741
WN2741
----
----
----
----
----
07:20
----
WN3107
WN507
WN507
07:35
07:30
07:30
07:35
07:35
----
----
WN3108
WN4286
WN4286
16:15
15:25
15:25
16:15
16:15
----
----
WN1652
WN4277
WN4277
----
----
----
----
----
----
16:25
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
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-22
