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Pittsburgh International (PIT) - Chicago Midway (CHI)

Here is the updated flight timetable for Pittsburgh International (PIT) - Chicago Midway (CHI) for 2025. Click on your desired route or flight to see detailed timetables and additional information.

The timetable shows local time!

WN 3264 Pittsburgh — Chicago
Southwest Airlines
Departure
05:40
Pittsburgh International
Flight time: 1 h 50 min
Arrival
06:30
Chicago Midway

Schedule: 11, 15, 16, 19, 25 January.

WN 2365 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
05:50
Pittsburgh International
Flight time: 1 h 45 min
Arrival
06:35
Chicago Midway

Schedule: 30 November.

WN 3264 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
05:50
Pittsburgh International
Flight time: 1 h 50 min
Arrival
06:40
Chicago Midway

Schedule: 6, 7, 8, 9, 12, 13, 14, 18, 20, 21, 22, 23, 26 January.

WN 2365 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:15
Pittsburgh International
Flight time: 1 h 40 min
Arrival
06:55
Chicago Midway

Schedule: 2, 3, 6, 7, 9, 10, 13, 14, 16, 21, 23, 24, 28 November, 7, 12, 14, 18 December, 5 January.

WN 2515 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:20
Pittsburgh International
Flight time: 1 h 30 min
Arrival
06:50
Chicago Midway

Schedule: daily, except for Sunday from 02.10 to 01.11.

WN 2365 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:20
Pittsburgh International
Flight time: 1 h 40 min
Arrival
07:00
Chicago Midway

Schedule: 22, 25, 26, 29 November, 1, 19, 20, 21, 22, 23, 26, 27, 28, 29, 30 December, 2, 3, 4 January.

WN 2593 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:25
Pittsburgh International
Flight time: 1 h 25 min
Arrival
06:50
Chicago Midway

Schedule: Monday, Thursday, Friday, Sunday from 07.08 to 29.09, except for 31.08.

WN 2489 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:25
Pittsburgh International
Flight time: 1 h 25 min
Arrival
06:50
Chicago Midway

Schedule: Sunday to 03.08.

WN 2489 Pittsburgh — Houston
Southwest Airlines Boeing 737
Departure
06:25
Pittsburgh International
Flight time: 1 h 25 min
Arrival
06:50
Chicago Midway

Schedule: Monday, Thursday, Friday from 05.06 to 04.08, except for 04.07.

WN 2489 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:30
Pittsburgh International
Flight time: 1 h 25 min
Arrival
06:55
Chicago Midway

Schedule: Tuesday, Wednesday, Saturday from 07.06 to 02.08.

WN 2515 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:35
Pittsburgh International
Flight time: 1 h 25 min
Arrival
07:00
Chicago Midway

Schedule: 5, 12, 19, 26 October.

WN 3264 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:35
Pittsburgh International
Flight time: 1 h 50 min
Arrival
07:25
Chicago Midway

Schedule: 10, 17, 24 January.

WN 3181 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:40
Pittsburgh International
Flight time: 1 h 40 min
Arrival
07:20
Chicago Midway

Schedule: 4, 5, 11, 12, 17, 18, 19, 20 November, 2, 3, 4, 5, 8, 9, 10, 11, 15, 16, 17, 24 December, ….

WN 3181 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:45
Pittsburgh International
Flight time: 1 h 40 min
Arrival
07:25
Chicago Midway

Schedule: 8, 15 November, 6, 13 December.

WN 1802 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
06:45
Pittsburgh International
Flight time: 1 h 30 min
Arrival
07:15
Chicago Midway

Schedule: 3, 4 June.

WN 2259 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:50
Pittsburgh International
Flight time: 1 h 40 min
Arrival
07:30
Chicago Midway

Schedule: 27 November.

WN 2593 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
06:55
Pittsburgh International
Flight time: 1 h 25 min
Arrival
07:20
Chicago Midway

Schedule: Saturday from 09.08 to 27.09.

WN 3557 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
06:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
07:25
Chicago Midway

Schedule: 4 July.

WN 287 Pittsburgh — Chicago
Southwest Airlines
Departure
07:00
Pittsburgh International
Flight time: 7 h 30 min
Arrival
13:30
Chicago Midway

Schedule: 4, 11, 18, 25 October, 1 November.

WN 4132 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
07:00
Pittsburgh International
Flight time: 1 h 25 min
Arrival
07:25
Chicago Midway

Schedule: Tuesday, Wednesday from 05.08 to 01.10.

WN 2515 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
07:10
Pittsburgh International
Flight time: 13 h 30 min
Arrival
19:40
Chicago Midway

Schedule: Sunday from 10.08 to 28.09, except for 31.08.

WN 2593 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
07:30
Pittsburgh International
Flight time: 1 h 25 min
Arrival
07:55
Chicago Midway

Schedule: 31 August.

WN 4324 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
09:40
Pittsburgh International
Flight time: 1 h 25 min
Arrival
10:05
Chicago Midway

Schedule: Monday, Thursday, Friday from 05.06 to 04.08, except for 04.07.

WN 2230 Pittsburgh — Kansas City
Southwest Airlines Boeing 737-800
Departure
09:45
Pittsburgh International
Flight time: 1 h 30 min
Arrival
10:15
Chicago Midway

Schedule: Tuesday, Wednesday from 07.10 to 29.10.

WN 3059 Pittsburgh — San Diego
Southwest Airlines Boeing 737-800
Departure
09:55
Pittsburgh International
Flight time: 1 h 25 min
Arrival
10:20
Chicago Midway

Schedule: Monday, Thursday, Friday from 02.10 to 31.10.

WN 836 Orlando — San Francisco
Southwest Airlines Boeing 737-700
Departure
10:10
Pittsburgh International
Flight time: 1 h 25 min
Arrival
10:35
Chicago Midway

Schedule: Monday, Thursday, Friday from 07.08 to 29.09.

WN 836 Pittsburgh — Los Angeles
Southwest Airlines Boeing 737
Departure
10:15
Pittsburgh International
Flight time: 1 h 25 min
Arrival
10:40
Chicago Midway

Schedule: Sunday from 10.08 to 28.09, except for 31.08.

WN 3343 Pittsburgh — Orlando
Southwest Airlines Boeing 737
Departure
10:30
Pittsburgh International
Flight time: 1 h 25 min
Arrival
10:55
Chicago Midway

Schedule: 5, 12, 19, 26 October.

WN 2593 Pittsburgh — Denver
Southwest Airlines Boeing 737-800
Departure
11:05
Pittsburgh International
Flight time: 1 h 25 min
Arrival
11:30
Chicago Midway

Schedule: Tuesday, Wednesday from 05.08 to 01.10.

WN 4324 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
11:10
Pittsburgh International
Flight time: 1 h 25 min
Arrival
11:35
Chicago Midway

Schedule: 4 July.

WN 2529 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
11:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
12:25
Chicago Midway

Schedule: 27 November.

WN 914 Fort Myers — Chicago
Southwest Airlines
Departure
12:15
Pittsburgh International
Flight time: 1 h 30 min
Arrival
12:45
Chicago Midway

Schedule: 6, 7, 8, 9, 12, 13, 14, 18, 20, 21, 22, 23, 26 January.

WN 4132 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
12:50
Pittsburgh International
Flight time: 1 h 25 min
Arrival
13:15
Chicago Midway

Schedule: 31 August.

WN 1052 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
13:05
Pittsburgh International
Flight time: 1 h 30 min
Arrival
13:35
Chicago Midway

Schedule: 3, 4 June.

WN 3265 Pittsburgh — Saint Louis
Southwest Airlines
Departure
13:25
Pittsburgh International
Flight time: 1 h 35 min
Arrival
14:00
Chicago Midway

Schedule: 11, 15, 16, 19, 25 January.

WN 2365 Orlando — San Francisco
Southwest Airlines Boeing 737-700
Departure
13:45
Pittsburgh International
Flight time: 1 h 25 min
Arrival
14:10
Chicago Midway

Schedule: Tuesday, Wednesday from 10.06 to 30.07.

WN 2365 Austin-Bergstrom — Chicago
Southwest Airlines
Departure
13:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
14:25
Chicago Midway

Schedule: 4, 5, 11, 12, 17, 18, 19, 20 November, 2, 3, 4, 5, 8, 9, 10, 11, 15, 16, 17, 24 December, ….

WN 2928 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
14:15
Pittsburgh International
Flight time: 1 h 30 min
Arrival
14:45
Chicago Midway

Schedule: 2, 3, 6, 7, 9, 10, 13, 14, 16, 21, 23, 24, 28 November, 7, 12, 14, 18 December, 5 January.

WN 4325 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
14:45
Pittsburgh International
Flight time: 1 h 25 min
Arrival
15:10
Chicago Midway

Schedule: Saturday to 02.08.

WN 2611 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
14:55
Pittsburgh International
Flight time: 1 h 25 min
Arrival
15:20
Chicago Midway

Schedule: Tuesday, Wednesday from 05.08 to 01.10.

WN 2928 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
15:00
Pittsburgh International
Flight time: 1 h 30 min
Arrival
15:30
Chicago Midway

Schedule: 30 November.

WN 681 Fresno — Chicago
Southwest Airlines Boeing 737-700
Departure
15:30
Pittsburgh International
Flight time: 1 h 30 min
Arrival
16:00
Chicago Midway

Schedule: Sunday to 03.08.

WN 1300 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
15:45
Pittsburgh International
Flight time: 1 h 25 min
Arrival
16:10
Chicago Midway

Schedule: Saturday from 09.08 to 27.09.

WN 4132 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
15:55
Pittsburgh International
Flight time: 1 h 25 min
Arrival
16:20
Chicago Midway

Schedule: Sunday from 10.08 to 28.09, except for 31.08.

WN 2928 Pittsburgh — San Francisco
Southwest Airlines Boeing 737
Departure
16:00
Pittsburgh International
Flight time: 1 h 25 min
Arrival
16:25
Chicago Midway

Schedule: Tuesday, Wednesday from 07.10 to 29.10.

WN 3042 Pittsburgh — Phoenix
Southwest Airlines Boeing 737-800
Departure
16:05
Pittsburgh International
Flight time: 1 h 30 min
Arrival
16:35
Chicago Midway

Schedule: 25, 26 November, 1, 19, 21, 22, 23, 26, 28, 29, 30 December, 2, 4 January.

WN 4132 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
16:15
Pittsburgh International
Flight time: 1 h 25 min
Arrival
16:40
Chicago Midway

Schedule: Monday, Thursday, Friday from 07.08 to 29.09.

WN 3343 Pittsburgh — Orlando
Southwest Airlines Boeing 737-800
Departure
16:35
Pittsburgh International
Flight time: 1 h 25 min
Arrival
17:00
Chicago Midway

Schedule: Monday, Thursday, Friday from 02.10 to 31.10.

WN 472 Washington — Chicago
Southwest Airlines
Departure
16:35
Pittsburgh International
Flight time: 1 h 25 min
Arrival
17:00
Chicago Midway

Schedule: 4, 11, 18, 25 October, 1 November.

WN 4325 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
17:00
Pittsburgh International
Flight time: 1 h 30 min
Arrival
17:30
Chicago Midway

Schedule: Monday, Thursday, Friday from 05.06 to 04.08, except for 04.07.

WN 4325 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
17:50
Pittsburgh International
Flight time: 1 h 30 min
Arrival
18:20
Chicago Midway

Schedule: 4 July.

WN 3067 Houston — Raleigh
Southwest Airlines
Departure
17:55
Pittsburgh International
Flight time: 1 h 25 min
Arrival
18:20
Chicago Midway

Schedule: 5, 12, 19, 26 October.

WN 1707 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
18:00
Pittsburgh International
Flight time: 1 h 35 min
Arrival
18:35
Chicago Midway

Schedule: 10, 17, 24 January.

WN 585 Washington — Chicago
Southwest Airlines
Departure
18:00
Pittsburgh International
Flight time: 1 h 35 min
Arrival
18:35
Chicago Midway

Schedule: 6, 7, 8, 9, 12, 13, 14, 18, 20, 21, 22, 23, 26 January.

WN 3634 Pittsburgh — Chicago
Southwest Airlines
Departure
18:05
Pittsburgh International
Flight time: 1 h 30 min
Arrival
18:35
Chicago Midway

Schedule: 8, 15 November, 6, 13 December.

WN 1300 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
18:40
Pittsburgh International
Flight time: 1 h 25 min
Arrival
19:05
Chicago Midway

Schedule: Tuesday, Wednesday from 05.08 to 01.10.

WN 3634 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
18:45
Pittsburgh International
Flight time: 1 h 30 min
Arrival
19:15
Chicago Midway

Schedule: 4, 5, 11, 12, 17, 18, 19, 20 November, 2, 3, 4, 5, 8, 9, 10, 11, 15, 16, 17, 24 December, ….

WN 3059 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
18:45
Pittsburgh International
Flight time: 1 h 30 min
Arrival
19:15
Chicago Midway

Schedule: Tuesday, Wednesday from 07.10 to 29.10.

WN 1300 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
18:50
Pittsburgh International
Flight time: 1 h 25 min
Arrival
19:15
Chicago Midway

Schedule: 31 August.

WN 1707 Sarasota — Chicago
Southwest Airlines
Departure
18:55
Pittsburgh International
Flight time: 1 h 35 min
Arrival
19:30
Chicago Midway

Schedule: 11, 15, 16, 19, 25 January.

WN 2611 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
19:00
Pittsburgh International
Flight time: 1 h 25 min
Arrival
19:25
Chicago Midway

Schedule: Monday, Thursday, Friday from 07.08 to 29.09.

WN 1300 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
19:05
Pittsburgh International
Flight time: 1 h 25 min
Arrival
19:30
Chicago Midway

Schedule: Sunday from 10.08 to 28.09, except for 31.08.

WN 1580 Pittsburgh — Chicago
Southwest Airlines Boeing 737-700
Departure
19:20
Pittsburgh International
Flight time: 1 h 30 min
Arrival
19:50
Chicago Midway

Schedule: 3, 4 June.

WN 2726 Pittsburgh — Chicago
Southwest Airlines Boeing 737-800
Departure
20:00
Pittsburgh International
Flight time: 1 h 30 min
Arrival
20:30
Chicago Midway

Schedule: Tuesday, Wednesday from 10.06 to 30.07.

WN 3634 Orlando — Chicago
Southwest Airlines
Departure
20:10
Pittsburgh International
Flight time: 1 h 30 min
Arrival
20:40
Chicago Midway

Schedule: 2, 3, 6, 7, 9, 10, 13, 14, 16, 21, 23, 24, 28 November, 7, 12, 14, 18 December, 5 January.

WN 2928 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
20:10
Pittsburgh International
Flight time: 1 h 30 min
Arrival
20:40
Chicago Midway

Schedule: Monday, Thursday, Friday from 02.10 to 31.10.

WN 2726 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
20:30
Pittsburgh International
Flight time: 1 h 30 min
Arrival
21:00
Chicago Midway

Schedule: Monday, Thursday, Friday, Saturday from 05.06 to 04.08, except for 04.07.

WN 3634 Orlando — Chicago
Southwest Airlines
Departure
20:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
21:25
Chicago Midway

Schedule: 30 November.

WN 2328 Denver — Chicago
Southwest Airlines
Departure
20:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
21:25
Chicago Midway

Schedule: 22, 29 November, 20, 27 December, 3 January.

WN 2328 Pittsburgh — Chicago
Southwest Airlines Boeing 737
Departure
20:55
Pittsburgh International
Flight time: 1 h 30 min
Arrival
21:25
Chicago Midway

Schedule: 25, 26 November, 1, 19, 21, 22, 23, 26, 28, 29, 30 December, 2, 4 January.

WN 3450 Pittsburgh — Omaha
Southwest Airlines Boeing 737-800
Departure
21:00
Pittsburgh International
Flight time: 1 h 30 min
Arrival
21:30
Chicago Midway

Schedule: Sunday to 03.08.

WN 1262 Austin-Bergstrom — Chicago
Southwest Airlines
Departure
21:30
Pittsburgh International
Flight time: 1 h 30 min
Arrival
22:00
Chicago Midway

Schedule: 5, 12, 19, 26 October.