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Chicago Midway (CHI) - Logan (BOS)

Here is the updated flight timetable for Chicago Midway (CHI) - Logan (BOS) 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
05:05
Flight time: 2 h 15 min
Arrival
08:20
Southwest Airlines Boeing 737
Departure
05:05
Flight time: 2 h 10 min
Arrival
08:15
Southwest Airlines Boeing 737
Departure
05:30
Flight time: 2 h 15 min
Arrival
08:45
Southwest Airlines Boeing 737-700
Departure
05:55
Flight time: 2 h 15 min
Arrival
09:10
Southwest Airlines Boeing 737
Departure
06:00
Flight time: 2 h 15 min
Arrival
09:15
Southwest Airlines Boeing 737-800
Departure
06:00
Flight time: 2 h 15 min
Arrival
09:15
Southwest Airlines Boeing 737-800
Departure
06:00
Flight time: 2 h 15 min
Arrival
09:15
Southwest Airlines Boeing 737
Departure
06:05
Flight time: 2 h 15 min
Arrival
09:20
Southwest Airlines Boeing 737-800
Departure
06:05
Flight time: 2 h 15 min
Arrival
09:20
Southwest Airlines
Departure
06:40
Flight time: 2 h 15 min
Arrival
09:55
Southwest Airlines Boeing 737-800
Departure
06:45
Flight time: 2 h 15 min
Arrival
10:00
Southwest Airlines
Departure
06:55
Flight time: 2 h 15 min
Arrival
10:10
Southwest Airlines Boeing 737-800
Departure
07:35
Flight time: 2 h 15 min
Arrival
10:50
Southwest Airlines Boeing 737-700
Departure
07:45
Flight time: 2 h 15 min
Arrival
11:00
Southwest Airlines Boeing 737
Departure
08:00
Flight time: 2 h 15 min
Arrival
11:15
Southwest Airlines Boeing 737-800
Departure
08:05
Flight time: 2 h 15 min
Arrival
11:20
Southwest Airlines Boeing 737-700
Departure
08:20
Flight time: 2 h 20 min
Arrival
11:40
Southwest Airlines Boeing 737-800
Departure
09:15
Flight time: 2 h 15 min
Arrival
12:30
Southwest Airlines
Departure
09:35
Flight time: 2 h 20 min
Arrival
12:55
Southwest Airlines Boeing 737
Departure
09:35
Flight time: 2 h 15 min
Arrival
12:50
Southwest Airlines Boeing 737-800
Departure
09:40
Flight time: 2 h 20 min
Arrival
13:00
Southwest Airlines Boeing 737
Departure
09:40
Flight time: 2 h 20 min
Arrival
13:00
Southwest Airlines Boeing 737-800
Departure
09:40
Flight time: 2 h 15 min
Arrival
12:55
Southwest Airlines Boeing 737-800
Departure
09:45
Flight time: 2 h 20 min
Arrival
13:05
Southwest Airlines Boeing 737
Departure
09:50
Flight time: 2 h 20 min
Arrival
13:10
Southwest Airlines Boeing 737
Departure
09:55
Flight time: 2 h 15 min
Arrival
13:10
Southwest Airlines Boeing 737-700
Departure
09:55
Flight time: 2 h 25 min
Arrival
13:20
Southwest Airlines Boeing 737
Departure
10:00
Flight time: 2 h 15 min
Arrival
13:15
Southwest Airlines Boeing 737-800
Departure
10:00
Flight time: 2 h 25 min
Arrival
13:25
Southwest Airlines Boeing 737-800
Departure
10:05
Flight time: 2 h 15 min
Arrival
13:20
Southwest Airlines Boeing 737-700
Departure
10:10
Flight time: 2 h 20 min
Arrival
13:30
Southwest Airlines Boeing 737
Departure
10:15
Flight time: 2 h 15 min
Arrival
13:30
Southwest Airlines Boeing 737-700
Departure
10:35
Flight time: 2 h 20 min
Arrival
13:55
Southwest Airlines Boeing 737
Departure
10:45
Flight time: 2 h 20 min
Arrival
14:05
Southwest Airlines Boeing 737
Departure
11:00
Flight time: 2 h 20 min
Arrival
14:20
Southwest Airlines Boeing 737
Departure
11:45
Flight time: 2 h 15 min
Arrival
15:00
Southwest Airlines Boeing 737
Departure
11:55
Flight time: 2 h 15 min
Arrival
15:10
Southwest Airlines Boeing 737-800
Departure
12:00
Flight time: 2 h 20 min
Arrival
15:20
Southwest Airlines Boeing 737-800
Departure
12:45
Flight time: 2 h 15 min
Arrival
16:00
Southwest Airlines Boeing 737-800
Departure
12:45
Flight time: 2 h 25 min
Arrival
16:10
Southwest Airlines Boeing 737
Departure
12:50
Flight time: 2 h 15 min
Arrival
16:05
Southwest Airlines Boeing 737-700
Departure
13:00
Flight time: 2 h 25 min
Arrival
16:25
Departure
13:15
Flight time: 2 h 15 min
Arrival
16:30
Southwest Airlines Boeing 737-800
Departure
13:15
Flight time: 2 h 20 min
Arrival
16:35
Southwest Airlines
Departure
13:20
Flight time: 3 h 55 min
Arrival
18:15
Southwest Airlines
Departure
13:20
Flight time: 3 h 55 min
Arrival
18:15
Southwest Airlines Boeing 737-700
Departure
13:25
Flight time: 2 h 20 min
Arrival
16:45
Southwest Airlines Boeing 737-800
Departure
13:30
Flight time: 2 h 15 min
Arrival
16:45
Southwest Airlines Boeing 737-800
Departure
13:40
Flight time: 2 h 15 min
Arrival
16:55
Southwest Airlines Boeing 737-800
Departure
13:45
Flight time: 2 h 25 min
Arrival
17:10
Southwest Airlines Boeing 737-800
Departure
13:55
Flight time: 2 h 25 min
Arrival
17:20
Southwest Airlines Boeing 737
Departure
13:55
Flight time: 2 h 15 min
Arrival
17:10
Southwest Airlines Boeing 737-800
Departure
14:00
Flight time: 2 h 10 min
Arrival
17:10
Southwest Airlines Boeing 737-800
Departure
14:10
Flight time: 2 h 20 min
Arrival
17:30
Southwest Airlines Boeing 737-800
Departure
14:20
Flight time: 2 h 15 min
Arrival
17:35
Southwest Airlines Boeing 737
Departure
14:35
Flight time: 2 h 20 min
Arrival
17:55
Southwest Airlines Boeing 737-800
Departure
15:10
Flight time: 2 h 15 min
Arrival
18:25
Southwest Airlines Boeing 737
Departure
15:10
Flight time: 2 h 20 min
Arrival
18:30
Southwest Airlines Boeing 737
Departure
15:30
Flight time: 2 h 15 min
Arrival
18:45
Southwest Airlines Boeing 737
Departure
15:35
Flight time: 2 h 20 min
Arrival
18:55
Southwest Airlines Boeing 737
Departure
15:40
Flight time: 2 h 20 min
Arrival
19:00
Southwest Airlines Boeing 737
Departure
15:55
Flight time: 2 h 20 min
Arrival
19:15
Southwest Airlines Boeing 737
Departure
16:05
Flight time: 2 h 15 min
Arrival
19:20
Southwest Airlines Boeing 737
Departure
16:45
Flight time: 2 h 20 min
Arrival
20:05
Southwest Airlines Boeing 737-800
Departure
17:30
Flight time: 2 h 20 min
Arrival
20:50
Southwest Airlines Boeing 737-800
Departure
17:35
Flight time: 2 h 15 min
Arrival
20:50
Southwest Airlines Boeing 737
Departure
17:35
Flight time: 2 h 15 min
Arrival
20:50
Southwest Airlines Boeing 737
Departure
17:35
Flight time: 2 h 15 min
Arrival
20:50
Southwest Airlines Boeing 737
Departure
17:40
Flight time: 2 h 15 min
Arrival
20:55
Southwest Airlines Boeing 737
Departure
17:40
Flight time: 2 h 20 min
Arrival
21:00
Southwest Airlines
Departure
17:45
Flight time: 2 h 20 min
Arrival
21:05
Southwest Airlines
Departure
17:45
Flight time: 26 h 20 min
Arrival
21:05
Departure
17:50
Flight time: 2 h 15 min
Arrival
21:05
Southwest Airlines Boeing 737-700
Departure
18:05
Flight time: 2 h 25 min
Arrival
21:30
Southwest Airlines Boeing 737
Departure
18:05
Flight time: 2 h 15 min
Arrival
21:20
Southwest Airlines Boeing 737-800
Departure
18:05
Flight time: 2 h 15 min
Arrival
21:20
Southwest Airlines Boeing 737
Departure
18:10
Flight time: 2 h 25 min
Arrival
21:35
Southwest Airlines Boeing 737-800
Departure
18:15
Flight time: 2 h 20 min
Arrival
21:35
Southwest Airlines Boeing 737-800
Departure
18:25
Flight time: 2 h 20 min
Arrival
21:45
Southwest Airlines Boeing 737
Departure
18:25
Flight time: 2 h 20 min
Arrival
21:45
Southwest Airlines
Departure
18:35
Flight time: 2 h 15 min
Arrival
21:50
Southwest Airlines Boeing 737-800
Departure
18:45
Flight time: 2 h 20 min
Arrival
22:05
Southwest Airlines Boeing 737
Departure
18:55
Flight time: 2 h 15 min
Arrival
22:10
Southwest Airlines Boeing 737
Departure
19:00
Flight time: 2 h 15 min
Arrival
22:15
Southwest Airlines Boeing 737
Departure
19:15
Flight time: 2 h 15 min
Arrival
22:30
Southwest Airlines Boeing 737-800
Departure
19:30
Flight time: 2 h 15 min
Arrival
22:45
Southwest Airlines
Departure
19:45
Flight time: 2 h 15 min
Arrival
23:00
Southwest Airlines Boeing 737
Departure
20:05
Flight time: 2 h 15 min
Arrival
23:20
Southwest Airlines Boeing 737-800
Departure
20:30
Flight time: 2 h 15 min
Arrival
23:45
Southwest Airlines Boeing 737-800
Departure
20:30
Flight time: 2 h 20 min
Arrival
23:50
Southwest Airlines Boeing 737-800
Departure
20:35
Flight time: 2 h 15 min
Arrival
23:50
Southwest Airlines Boeing 737-700
Departure
20:35
Flight time: 2 h 20 min
Arrival
23:55
Southwest Airlines Boeing 737-800
Departure
21:20
Flight time: 2 h 20 min
Arrival
00:40
Southwest Airlines
Departure
21:45
Flight time: 2 h 15 min
Arrival
01:00
Southwest Airlines Boeing 737-700
Departure
22:00
Flight time: 2 h 15 min
Arrival
01:15