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Flights
San Diego (SAN) - Chicago Midway (CHI)

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

The timetable shows local time!

Southwest Airlines Boeing 737
Departure
06:25
Flight time: 4 h 0 min
Arrival
12:25
Southwest Airlines Boeing 737-700
Departure
06:30
Flight time: 6 h 15 min
Arrival
14:45
Southwest Airlines Boeing 737
Departure
06:30
Flight time: 4 h 5 min
Arrival
12:35
Southwest Airlines Boeing 737
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737-700
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737-800
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737-800
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737-800
Departure
06:35
Flight time: 4 h 5 min
Arrival
12:40
Southwest Airlines Boeing 737
Departure
06:40
Flight time: 4 h 5 min
Arrival
12:45
Southwest Airlines Boeing 737
Departure
06:45
Flight time: 6 h 30 min
Arrival
15:15
Southwest Airlines Boeing 737
Departure
06:45
Flight time: 3 h 55 min
Arrival
12:40
Southwest Airlines Boeing 737
Departure
06:50
Flight time: 4 h 5 min
Arrival
12:55
Southwest Airlines Boeing 737
Departure
06:55
Flight time: 4 h 0 min
Arrival
12:55
Southwest Airlines Boeing 737-800
Departure
06:55
Flight time: 4 h 5 min
Arrival
13:00
Southwest Airlines Boeing 737-700
Departure
06:55
Flight time: 4 h 0 min
Arrival
12:55
Southwest Airlines Boeing 737
Departure
07:00
Flight time: 4 h 0 min
Arrival
13:00
Southwest Airlines Boeing 737-700
Departure
07:00
Flight time: 4 h 10 min
Arrival
13:10
Southwest Airlines Boeing 737-800
Departure
07:10
Flight time: 4 h 0 min
Arrival
13:10
Southwest Airlines Boeing 737-700
Departure
07:20
Flight time: 4 h 5 min
Arrival
13:25
Southwest Airlines Boeing 737
Departure
07:25
Flight time: 3 h 55 min
Arrival
13:20
Southwest Airlines Boeing 737-700
Departure
07:30
Flight time: 4 h 0 min
Arrival
13:30
Southwest Airlines Boeing 737-700
Departure
07:35
Flight time: 3 h 55 min
Arrival
13:30
Southwest Airlines Boeing 737
Departure
08:10
Flight time: 4 h 0 min
Arrival
14:10
Southwest Airlines Boeing 737-700
Departure
08:15
Flight time: 4 h 5 min
Arrival
14:20
Southwest Airlines Boeing 737-700
Departure
08:40
Flight time: 7 h 35 min
Arrival
18:15
Southwest Airlines Boeing 737-700
Departure
09:05
Flight time: 6 h 5 min
Arrival
17:10
Southwest Airlines Boeing 737-700
Departure
09:10
Flight time: 6 h 5 min
Arrival
17:15
Southwest Airlines Boeing 737-800
Departure
09:20
Flight time: 7 h 30 min
Arrival
18:50
Southwest Airlines Boeing 737-700
Departure
09:20
Flight time: 6 h 5 min
Arrival
17:25
Southwest Airlines Boeing 737-700
Departure
09:30
Flight time: 8 h 5 min
Arrival
19:35
Southwest Airlines Boeing 737-700
Departure
09:35
Flight time: 6 h 40 min
Arrival
18:15
Southwest Airlines Boeing 737-700
Departure
10:05
Flight time: 8 h 20 min
Arrival
20:25
Southwest Airlines Boeing 737
Departure
10:05
Flight time: 4 h 0 min
Arrival
16:05
Southwest Airlines
Departure
10:25
Flight time: 4 h 0 min
Arrival
16:25
Southwest Airlines Boeing 737-800
Departure
10:35
Flight time: 4 h 0 min
Arrival
16:35
Southwest Airlines Boeing 737-800
Departure
10:35
Flight time: 3 h 55 min
Arrival
16:30
Southwest Airlines Boeing 737-800
Departure
10:40
Flight time: 4 h 0 min
Arrival
16:40
Southwest Airlines Boeing 737-800
Departure
10:45
Flight time: 4 h 0 min
Arrival
16:45
Southwest Airlines Boeing 737
Departure
10:50
Flight time: 4 h 0 min
Arrival
16:50
Southwest Airlines Boeing 737
Departure
11:00
Flight time: 4 h 0 min
Arrival
17:00
Southwest Airlines Boeing 737
Departure
11:00
Flight time: 4 h 10 min
Arrival
17:10
Southwest Airlines Boeing 737-700
Departure
11:00
Flight time: 4 h 0 min
Arrival
17:00
Southwest Airlines Boeing 737
Departure
11:05
Flight time: 7 h 50 min
Arrival
20:55
Southwest Airlines
Departure
11:10
Flight time: 5 h 20 min
Arrival
18:30
Southwest Airlines Boeing 737-700
Departure
11:20
Flight time: 4 h 0 min
Arrival
17:20
Southwest Airlines Boeing 737-700
Departure
11:20
Flight time: 6 h 20 min
Arrival
19:40
Southwest Airlines Boeing 737-800
Departure
11:25
Flight time: 4 h 0 min
Arrival
17:25
Southwest Airlines
Departure
11:35
Flight time: 7 h 50 min
Arrival
21:25
Southwest Airlines Boeing 737
Departure
11:55
Flight time: 4 h 5 min
Arrival
18:00
Southwest Airlines Boeing 737-700
Departure
12:00
Flight time: 4 h 5 min
Arrival
18:05
Southwest Airlines Boeing 737
Departure
12:05
Flight time: 4 h 5 min
Arrival
18:10
Departure
12:05
Flight time: 4 h 5 min
Arrival
18:10
Southwest Airlines Boeing 737
Departure
12:20
Flight time: 4 h 5 min
Arrival
18:25
Southwest Airlines Boeing 737
Departure
12:55
Flight time: 4 h 0 min
Arrival
18:55
Southwest Airlines Boeing 737
Departure
13:20
Flight time: 4 h 5 min
Arrival
19:25
Southwest Airlines Boeing 737-800
Departure
13:30
Flight time: 4 h 0 min
Arrival
19:30
Southwest Airlines Boeing 737
Departure
13:40
Flight time: 4 h 0 min
Arrival
19:40
Southwest Airlines Boeing 737
Departure
13:45
Flight time: 4 h 0 min
Arrival
19:45
Southwest Airlines Boeing 737-700
Departure
13:50
Flight time: 4 h 0 min
Arrival
19:50
Southwest Airlines Boeing 737-700
Departure
14:15
Flight time: 3 h 55 min
Arrival
20:10
Southwest Airlines Boeing 737
Departure
14:50
Flight time: 5 h 20 min
Arrival
22:10
Southwest Airlines Boeing 737-700
Departure
15:10
Flight time: 4 h 0 min
Arrival
21:10
Southwest Airlines Boeing 737-700
Departure
15:35
Flight time: 3 h 55 min
Arrival
21:30
Southwest Airlines Boeing 737-700
Departure
16:00
Flight time: 4 h 0 min
Arrival
22:00
Southwest Airlines Boeing 737-700
Departure
16:05
Flight time: 3 h 55 min
Arrival
22:00
Southwest Airlines Boeing 737
Departure
16:15
Flight time: 5 h 25 min
Arrival
23:40
Southwest Airlines Boeing 737-700
Departure
16:20
Flight time: 27 h 15 min
Arrival
21:35
Southwest Airlines Boeing 737-800
Departure
16:50
Flight time: 4 h 0 min
Arrival
22:50
Southwest Airlines Boeing 737
Departure
17:00
Flight time: 3 h 55 min
Arrival
22:55
Southwest Airlines Boeing 737-800
Departure
17:15
Flight time: 5 h 40 min
Arrival
00:55
Southwest Airlines Boeing 737-700
Departure
17:35
Flight time: 4 h 0 min
Arrival
23:35
Southwest Airlines Boeing 737
Departure
17:35
Flight time: 4 h 0 min
Arrival
23:35
Southwest Airlines Boeing 737
Departure
17:45
Flight time: 4 h 0 min
Arrival
23:45
Southwest Airlines Boeing 737
Departure
17:50
Flight time: 5 h 20 min
Arrival
01:10
Southwest Airlines Boeing 737-700
Departure
17:55
Flight time: 4 h 0 min
Arrival
23:55
Southwest Airlines Boeing 737
Departure
17:55
Flight time: 4 h 0 min
Arrival
23:55
Southwest Airlines Boeing 737
Departure
18:25
Flight time: 4 h 0 min
Arrival
00:25
Southwest Airlines Boeing 737
Departure
18:25
Flight time: 4 h 0 min
Arrival
00:25
Southwest Airlines Boeing 737-700
Departure
18:30
Flight time: 4 h 0 min
Arrival
00:30
Southwest Airlines Boeing 737-800
Departure
18:30
Flight time: 3 h 55 min
Arrival
00:25
Southwest Airlines
Departure
18:35
Flight time: 4 h 0 min
Arrival
00:35
Southwest Airlines Boeing 737-800
Departure
18:45
Flight time: 4 h 0 min
Arrival
00:45
Southwest Airlines Boeing 737-800
Departure
18:45
Flight time: 3 h 55 min
Arrival
00:40
Southwest Airlines Boeing 737-700
Departure
18:55
Flight time: 3 h 55 min
Arrival
00:50
Southwest Airlines Boeing 737
Departure
19:00
Flight time: 3 h 55 min
Arrival
00:55
Southwest Airlines Boeing 737
Departure
19:15
Flight time: 3 h 55 min
Arrival
01:10
Southwest Airlines Boeing 737-800
Departure
19:35
Flight time: 3 h 55 min
Arrival
01:30