All airlines flying from Pensacola (PNS) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sat 16:15 Pensacola (PNS) 18:35 Chicago Midway (MDW) Southwest Airlines WN 745 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-03-07 through 2026-04-04
Sun 16:50 Pensacola (PNS) 19:05 Chicago Midway (MDW) Southwest Airlines WN 1083 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 16:50 Pensacola (PNS) 19:05 Chicago Midway (MDW) Southwest Airlines WN 1083 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-05-31
Sat 15:50 Pensacola (PNS) 18:05 Chicago Midway (MDW) Southwest Airlines WN 1147 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 17:25 Pensacola (PNS) 19:40 Chicago Midway (MDW) Southwest Airlines WN 1929 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-05 through 2026-04-06
Sun 17:35 Pensacola (PNS) 19:50 Chicago Midway (MDW) Southwest Airlines WN 2474 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-07 through 2026-08-02
Tue,Wed 15:45 Pensacola (PNS) 18:00 Chicago Midway (MDW) Southwest Airlines WN 2701 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 10:40 Pensacola (PNS) 12:55 Chicago Midway (MDW) Southwest Airlines WN 2866 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-04 through 2026-08-03
Sun 17:05 Pensacola (PNS) 19:20 Chicago Midway (MDW) Southwest Airlines WN 3057 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-05-24
Sat 14:50 Pensacola (PNS) 17:10 Chicago Midway (MDW) Southwest Airlines WN 3850 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-11 through 2026-05-30
Tue,Wed 17:20 Pensacola (PNS) 19:35 Chicago Midway (MDW) Southwest Airlines WN 4089 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-10 through 2026-04-01
Sat 10:20 Pensacola (PNS) 12:35 Chicago Midway (MDW) Southwest Airlines WN 4580 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-07 through 2026-04-04
Sun 18:10 Pensacola (PNS) 20:25 Chicago Midway (MDW) Southwest Airlines WN 4580 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-08 through 2026-04-05
Non-Direct Flights:
Thu,Fri,Sun 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-01-11 through 2026-01-16
Mon,Sun 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-01 through 2026-02-06
Mon,Sun 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-17 through 2026-02-23
Mon 16:25 Pensacola (PNS) 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Operates only on 2026-03-02
Sat 14:20 Pensacola (PNS) 17:50 Chicago Midway (MDW) Southwest Airlines WN 373 1-stop Boeing 737-700 (Scimitar Winglets) 3:30 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 10:00 Pensacola (PNS) 14:45 Chicago Midway (MDW) Southwest Airlines WN 2111 1-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2026-03-05 through 2026-04-06
Fri,Sun 18:10 Pensacola (PNS) 22:50 Chicago Midway (MDW) Southwest Airlines WN 2143 1-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-01-02 through 2026-01-04
Mon,Thu 16:35 Pensacola (PNS) 22:35 Chicago Midway (MDW) Southwest Airlines WN 943 2-stop Boeing 737-700 (Scimitar Winglets) 6:00 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 16:35 Pensacola (PNS) 22:35 Chicago Midway (MDW) Southwest Airlines WN 943 2-stop Boeing 737-700 (Scimitar Winglets) 6:00 Effective 2026-02-20 through 2026-03-01

A domestic route departing from the Pensacola airport (PNS) and arriving at Chicago Midway airport (MDW).
The flight distance is 782 miles, or 1258 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 2:15 and 2:20.

Return (MDW-PNS) flights

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All airlines flying from Pensacola (PNS) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN745

16:15

Pensacola (PNS)

18:35

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1083

16:50

Pensacola (PNS)

19:05

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1083

16:50

Pensacola (PNS)

19:05

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1147

15:50

Pensacola (PNS)

18:05

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1929

17:25

Pensacola (PNS)

19:40

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2474

17:35

Pensacola (PNS)

19:50

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2701

15:45

Pensacola (PNS)

18:00

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2866

10:40

Pensacola (PNS)

12:55

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3057

17:05

Pensacola (PNS)

19:20

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3850

14:50

Pensacola (PNS)

17:10

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4089

17:20

Pensacola (PNS)

19:35

Chicago Midway (MDW)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4580

10:20

Pensacola (PNS)

12:35

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4580

18:10

Pensacola (PNS)

20:25

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

16:25

Pensacola (PNS)

20:10

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN373

14:20

Pensacola (PNS)

17:50

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2111

10:00

Pensacola (PNS)

14:45

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2143

18:10

Pensacola (PNS)

22:50

Chicago Midway (MDW)

Effective 2026-01-02 through 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN943

16:35

Pensacola (PNS)

22:35

Chicago Midway (MDW)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:00, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN943

16:35

Pensacola (PNS)

22:35

Chicago Midway (MDW)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:00, 2-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Pensacola airport (PNS) and arriving at Chicago Midway airport (MDW).
The flight distance is 782 miles, or 1258 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 2:15 and 2:20.

Return (MDW-PNS) flights

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