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.
Choose airline
Schedules
Non-stop with Southwest Airlines
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Total flight time: 1 hour and 55 minutes
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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10 flights per week
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Boeing 737MAX 8 PassengerBoeing 737-700 (winglets) Passenger/BBJ1
OKC
Direct
MDW
W7, Feb 10 - Feb 16
Flight
Mon
Feb 10
Tue
Feb 11
Wed
Feb 12
Thu
Feb 13
Fri
Feb 14
Sat
Feb 15
Sun
Feb 16
WN964
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----
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05:05
05:05
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05:05
WN2418
05:40
07:20
07:20
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----
----
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WN1722
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----
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----
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14:20
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The timetable & schedule information was updated at 2025-01-15
Via Saint Louis with Southwest Airlines
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Total flight time: 3h 10m - 5h 35m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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12 flights per week
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Boeing 737MAX 8 PassengerBoeing 737-700 (winglets) Passenger/BBJ1
OKC
Via STL
MDW
W7, Feb 10 - Feb 16
Flight
Mon
Feb 10
Tue
Feb 11
Wed
Feb 12
Thu
Feb 13
Fri
Feb 14
Sat
Feb 15
Sun
Feb 16
WN1707
WN4153
WN4153
----
----
----
----
----
06:00
----
WN1707
WN2364
WN2364
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06:45
06:45
----
----
----
----
WN2713
WN3079
WN3079
----
----
----
----
----
11:00
----
WN3350
WN3079
WN3079
----
----
----
12:55
12:55
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12:55
WN3904
WN1253
WN1253
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15:50
15:50
----
----
----
----
WN543
WN491
WN491
----
----
----
----
----
16:30
----
WN543
WN1253
WN1253
----
----
----
----
----
16:30
----
WN3904
WN3012
WN3012
17:00
----
----
----
----
----
----
WN3904
WN2455
WN2455
----
----
----
18:00
18:00
----
18:00
The timetable & schedule information was updated at 2025-01-15
Via Minneapolis with Delta Air Lines
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Total flight time: 5h 27m - 5h 50m.
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Sky Team Alliance
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6 flights per week
OKC
Via MSP
MDW
W7, Feb 10 - Feb 16
Flight
Mon
Feb 10
Tue
Feb 11
Wed
Feb 12
Thu
Feb 13
Fri
Feb 14
Sat
Feb 15
Sun
Feb 16
DL3844
DL3792
DL3792
07:15
07:15
07:15
07:15
07:15
----
----
The timetable & schedule information was updated at 2025-01-15
Via Minneapolis with Southwest Airlines
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Total flight time: 7h 30m - 7h 30m.
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Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
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3 flights per week
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Boeing 737MAX 8 PassengerBoeing 737-700 (winglets) Passenger/BBJ1
OKC
Via MSP
MDW
W7, Feb 10 - Feb 16
Flight
Mon
Feb 10
Tue
Feb 11
Wed
Feb 12
Thu
Feb 13
Fri
Feb 14
Sat
Feb 15
Sun
Feb 16
WN1707
WN4153
WN4153
----
----
----
----
----
06:00
----
WN1707
WN2364
WN2364
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06:45
06:45
----
----
----
----
WN2713
WN3079
WN3079
----
----
----
----
----
11:00
----
WN3350
WN3079
WN3079
----
----
----
12:55
12:55
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12:55
WN3904
WN1253
WN1253
----
15:50
15:50
----
----
----
----
WN543
WN491
WN491
----
----
----
----
----
16:30
----
WN543
WN1253
WN1253
----
----
----
----
----
16:30
----
WN3904
WN3012
WN3012
17:00
----
----
----
----
----
----
WN3904
WN2455
WN2455
----
----
----
18:00
18:00
----
18:00
The timetable & schedule information was updated at 2025-01-15
Via Nashville with Southwest Airlines
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Total flight time: 3h 55m - 6h 15m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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1 flights per week
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Boeing 737MAX 8 PassengerBoeing 737-700 (winglets) Passenger/BBJ1
OKC
Via BNA
MDW
W7, Feb 10 - Feb 16
Flight
Mon
Feb 10
Tue
Feb 11
Wed
Feb 12
Thu
Feb 13
Fri
Feb 14
Sat
Feb 15
Sun
Feb 16
WN1707
WN4153
WN4153
----
----
----
----
----
06:00
----
WN1707
WN2364
WN2364
----
06:45
06:45
----
----
----
----
WN2713
WN3079
WN3079
----
----
----
----
----
11:00
----
WN3350
WN3079
WN3079
----
----
----
12:55
12:55
----
12:55
WN3904
WN1253
WN1253
----
15:50
15:50
----
----
----
----
WN543
WN491
WN491
----
----
----
----
----
16:30
----
WN543
WN1253
WN1253
----
----
----
----
----
16:30
----
WN3904
WN3012
WN3012
17:00
----
----
----
----
----
----
WN3904
WN2455
WN2455
----
----
----
18:00
18:00
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18:00
The timetable & schedule information was updated at 2025-01-15