All airlines flying from Boston Logan (BOS) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sat
14:10
Boston Logan (BOS) B
15:50
Chicago Midway (MDW) Southwest Airlines WN 746 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
15:20
Boston Logan (BOS) B
16:55
Chicago Midway (MDW) Southwest Airlines WN 746 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
17:55
Boston Logan (BOS) B
19:35
Chicago Midway (MDW) Southwest Airlines WN 746 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-08-06 through 2026-09-28 |
| Sun
10:35
Boston Logan (BOS) B
12:15
Chicago Midway (MDW) Southwest Airlines WN 776 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-12 through 2026-05-17 |
| Sun
10:35
Boston Logan (BOS) B
12:15
Chicago Midway (MDW) Southwest Airlines WN 776 Non-stop Boeing 737-800 (73H) 2:40 Operates only on 2026-05-31 |
| Mon,Thu,Fri
10:40
Boston Logan (BOS) B
12:20
Chicago Midway (MDW) Southwest Airlines WN 776 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
10:45
Boston Logan (BOS) B
12:25
Chicago Midway (MDW) Southwest Airlines WN 776 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-07 through 2026-06-03 |
| Sat
06:30
Boston Logan (BOS) B
08:20
Chicago Midway (MDW) Southwest Airlines WN 833 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-03-07 through 2026-04-04 |
| Sun
07:05
Boston Logan (BOS) B
09:00
Chicago Midway (MDW) Southwest Airlines WN 833 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-08 through 2026-04-05 |
| Mon-Fri
07:15
Boston Logan (BOS) B
09:10
Chicago Midway (MDW) Southwest Airlines WN 833 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-05 through 2026-04-06 |
| Sat
13:50
Boston Logan (BOS) B
15:30
Chicago Midway (MDW) Southwest Airlines WN 898 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-11 through 2026-05-30 |
| Tue,Wed
14:25
Boston Logan (BOS) B
16:05
Chicago Midway (MDW) Southwest Airlines WN 898 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
15:45
Boston Logan (BOS) B
17:30
Chicago Midway (MDW) Southwest Airlines WN 898 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-04-09 through 2026-06-01 |
| Mon,Thu,Fri
07:10
Boston Logan (BOS) B
09:00
Chicago Midway (MDW) Southwest Airlines WN 961 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-09 through 2026-06-01 |
| Sat
07:15
Boston Logan (BOS) B
09:05
Chicago Midway (MDW) Southwest Airlines WN 961 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-11 through 2026-05-30 |
| Tue,Wed
07:20
Boston Logan (BOS) B
09:05
Chicago Midway (MDW) Southwest Airlines WN 961 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-04-07 through 2026-06-03 |
| Mon
18:55
Boston Logan (BOS) B
20:45
Chicago Midway (MDW) Southwest Airlines WN 1030 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-01-05 |
| Tue,Wed
18:00
Boston Logan (BOS) B
19:50
Chicago Midway (MDW) Southwest Airlines WN 1266 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
18:25
Boston Logan (BOS) B
20:25
Chicago Midway (MDW) Southwest Airlines WN 1266 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-05 through 2026-04-06 |
| Sat,Sun
18:35
Boston Logan (BOS) B
20:30
Chicago Midway (MDW) Southwest Airlines WN 1266 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-07 through 2026-04-05 |
| Mon,Tue,Fri,Sun
05:15
Boston Logan (BOS) B
07:00
Chicago Midway (MDW) Southwest Airlines WN 1430 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Valid until 2026-01-04 |
| Sat
05:20
Boston Logan (BOS) B
07:05
Chicago Midway (MDW) Southwest Airlines WN 1430 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Valid until 2026-01-03 |
| Wed,Thu
05:30
Boston Logan (BOS) B
07:15
Chicago Midway (MDW) Southwest Airlines WN 1432 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Valid until 2026-01-01 |
| Mon
13:45
Boston Logan (BOS) B
15:30
Chicago Midway (MDW) Southwest Airlines WN 1432 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2026-01-05 |
| Mon,Tue,Fri,Sun
14:25
Boston Logan (BOS) B
16:10
Chicago Midway (MDW) Southwest Airlines WN 1432 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2026-01-04 |
| Sat
18:05
Boston Logan (BOS) B
19:55
Chicago Midway (MDW) Southwest Airlines WN 1436 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-03 |
| Fri,Sun
18:50
Boston Logan (BOS) B
20:45
Chicago Midway (MDW) Southwest Airlines WN 1436 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-01-02 through 2026-01-04 |
| Sun
09:15
Boston Logan (BOS) B
10:50
Chicago Midway (MDW) Southwest Airlines WN 1585 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-08-09 through 2026-09-27 |
| Tue,Wed
10:05
Boston Logan (BOS) B
11:35
Chicago Midway (MDW) Southwest Airlines WN 1645 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-04 through 2026-09-30 |
| Mon
05:15
Boston Logan (BOS) B
07:00
Chicago Midway (MDW) Southwest Airlines WN 2012 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Operates only on 2026-01-05 |
| Wed,Thu
13:35
Boston Logan (BOS) B
15:20
Chicago Midway (MDW) Southwest Airlines WN 2012 Non-stop Boeing 737-700 (73W) 2:45 Valid until 2026-01-01 |
| Mon,Thu,Fri
12:40
Boston Logan (BOS) B
14:10
Chicago Midway (MDW) Southwest Airlines WN 2421 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-06 through 2026-09-28 |
| Sat
09:25
Boston Logan (BOS) B
11:05
Chicago Midway (MDW) Southwest Airlines WN 2540 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-04-11 through 2026-05-30 |
| Sun
21:05
Boston Logan (BOS) B
22:40
Chicago Midway (MDW) Southwest Airlines WN 2662 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-08-09 through 2026-09-27 |
| Sun
16:45
Boston Logan (BOS) B
18:35
Chicago Midway (MDW) Southwest Airlines WN 2777 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
05:35
Boston Logan (BOS) B
07:10
Chicago Midway (MDW) Southwest Airlines WN 3054 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
20:05
Boston Logan (BOS) B
21:45
Chicago Midway (MDW) Southwest Airlines WN 3183 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-08-06 through 2026-09-28 |
| Sat
05:20
Boston Logan (BOS) B
06:55
Chicago Midway (MDW) Southwest Airlines WN 3239 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
05:25
Boston Logan (BOS) B
07:00
Chicago Midway (MDW) Southwest Airlines WN 3239 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-06-04 through 2026-08-03 |
| Sun
06:10
Boston Logan (BOS) B
07:55
Chicago Midway (MDW) Southwest Airlines WN 3285 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-04-12 through 2026-05-17 |
| Sun
06:10
Boston Logan (BOS) B
07:55
Chicago Midway (MDW) Southwest Airlines WN 3285 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2026-05-31 |
| Sun
08:10
Boston Logan (BOS) B
09:55
Chicago Midway (MDW) Southwest Airlines WN 3285 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Operates only on 2026-05-24 |
| Sun
19:05
Boston Logan (BOS) B
20:55
Chicago Midway (MDW) Southwest Airlines WN 3287 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-07 through 2026-08-02 |
| Sat
15:25
Boston Logan (BOS) B
17:00
Chicago Midway (MDW) Southwest Airlines WN 3480 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-08 through 2026-09-26 |
| Sun
13:45
Boston Logan (BOS) B
15:30
Chicago Midway (MDW) Southwest Airlines WN 3514 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
14:00
Boston Logan (BOS) B
15:45
Chicago Midway (MDW) Southwest Airlines WN 3514 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
15:10
Boston Logan (BOS) B
16:55
Chicago Midway (MDW) Southwest Airlines WN 3514 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-03-05 through 2026-04-06 |
| Sun
13:55
Boston Logan (BOS) B
15:35
Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-04-12 through 2026-05-17 |
| Sun
13:55
Boston Logan (BOS) B
15:35
Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Operates only on 2026-05-31 |
| Sun
14:20
Boston Logan (BOS) B
16:00
Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Operates only on 2026-05-24 |
- A domestic route departing from the Boston Logan airport (BOS) and arriving at Chicago Midway airport (MDW).
- The flight distance is 858 miles, or 1380 km.
- The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
- For direct flights, the flight time varies between 2:30 and 3:00.
