Airlines with flights from Pensacola to Chicago
There are two airlines with scheduled flights between PNS and MDW. Southwest is the only airline with non-stop flights from Pensacola Rgnl to Midway International Airport and the flight time is 2 hours and 15 minutes.
There are two airlines with scheduled flights between PNS and MDW. Southwest is the only airline with non-stop flights from Pensacola Rgnl to Midway International Airport and the flight time is 2 hours and 15 minutes. Choose airline
Direct
Non-stop
2h 15min
Via Saint Louis
3h 30min
Via Nashville
3h 35min
Via Atlanta
3h 50min
Via Kansas City
4h 25min
Via Detroit
4h 55min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 15 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
7 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
PNS
Direct
MDW
W27, Jun 29 - Jul 05
Flight
Mon
Jun 29
Tue
Jun 30
Wed
Jul 1
Thu
Jul 2
Fri
Jul 3
Sat
Jul 4
Sun
Jul 5
WN2866
10:40
----
----
10:40
10:40
----
----
WN1147
----
----
----
----
----
12:50
----
WN2701
----
15:45
15:45
----
----
----
----
WN2474
----
----
----
----
----
----
17:35
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 3h 30m - 6h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
12 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
PNS
Via STL
MDW
W27, Jun 29 - Jul 05
Flight
Mon
Jun 29
Tue
Jun 30
Wed
Jul 1
Thu
Jul 2
Fri
Jul 3
Sat
Jul 4
Sun
Jul 5
WN4979
WN556
WN556
11:55
----
----
11:55
11:55
----
----
WN276
WN860
WN860
----
----
----
----
----
14:00
----
WN2533
WN3957
WN3957
----
18:40
18:40
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 3h 35m - 7h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
92 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
PNS
Via BNA
MDW
W27, Jun 29 - Jul 05
Flight
Mon
Jun 29
Tue
Jun 30
Wed
Jul 1
Thu
Jul 2
Fri
Jul 3
Sat
Jul 4
Sun
Jul 5
WN3391
WN347
WN347
----
----
----
----
----
06:50
----
WN3391
WN507
WN507
07:50
07:50
07:50
07:50
07:50
----
----
WN2463
WN4005
WN4005
----
----
----
----
----
16:10
----
WN1657
WN4286
WN4286
----
17:30
17:30
----
----
----
----
WN2264
WN4286
WN4286
18:20
----
----
18:20
18:20
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 3h 50m - 6h 11m.
-
Sky Team Alliance
-
102 flights per week
PNS
Via ATL
MDW
W27, Jun 29 - Jul 05
Flight
Mon
Jun 29
Tue
Jun 30
Wed
Jul 1
Thu
Jul 2
Fri
Jul 3
Sat
Jul 4
Sun
Jul 5
DL3019
DL1063
DL1063
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL3129
DL2417
DL2417
07:00
07:00
07:00
07:00
07:00
----
07:00
DL3067
DL2417
DL2417
08:00
08:00
08:00
08:00
08:00
----
08:00
DL3198
DL1728
DL1728
11:40
11:57
11:57
11:57
11:57
----
11:57
DL3198
DL2417
DL2417
----
----
----
----
----
11:40
----
DL1013
DL1076
DL1076
16:22
16:25
16:25
16:22
16:22
16:27
16:25
DL2211
DL1076
DL1076
18:11
18:11
18:11
18:11
18:11
----
18:11
The timetable & schedule information was updated at 2026-04-21
Via Kansas City with Southwest Airlines
-
Total flight time: 4h 25m - 6h 10m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
10 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
PNS
Via MCI
MDW
W27, Jun 29 - Jul 05
Flight
Mon
Jun 29
Tue
Jun 30
Wed
Jul 1
Thu
Jul 2
Fri
Jul 3
Sat
Jul 4
Sun
Jul 5
WN4850
WN2571
WN2571
----
----
----
----
----
----
11:20
WN4795
WN2029
WN2029
14:10
----
----
14:10
14:10
----
----
The timetable & schedule information was updated at 2026-04-21
