All airlines flying from Midway, Chicago (MDW) to Boston Logan (BOS).

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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 08:00 Midway, Chicago (MDW) 11:15 Boston Logan (BOS) B
Southwest Airlines WN 171 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-06-08 through 2025-08-03
Tue,Wed 09:45 Midway, Chicago (MDW) 13:05 Boston Logan (BOS) B
Southwest Airlines WN 171 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 10:35 Midway, Chicago (MDW) 13:55 Boston Logan (BOS) B
Southwest Airlines WN 171 Non-stop Boeing 737-700 (73W) 2:20 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 10:35 Midway, Chicago (MDW) 13:55 Boston Logan (BOS) B
Southwest Airlines WN 171 Non-stop Boeing 737-700 (73W) 2:20 Effective 2025-07-07 through 2025-08-04
Tue,Wed 09:55 Midway, Chicago (MDW) 13:20 Boston Logan (BOS) B
Southwest Airlines WN 278 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-05 through 2025-10-01
Mon,Thu,Fri 12:00 Midway, Chicago (MDW) 15:20 Boston Logan (BOS) B
Southwest Airlines WN 278 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-08-07 through 2025-09-29
Mon,Thu,Fri 05:30 Midway, Chicago (MDW) 08:45 Boston Logan (BOS) B
Southwest Airlines WN 404 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2025-06-02
Sat 07:50 Midway, Chicago (MDW) 11:05 Boston Logan (BOS) B
Southwest Airlines WN 404 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2025-05-31
Sun 15:45 Midway, Chicago (MDW) 19:05 Boston Logan (BOS) B
Southwest Airlines WN 483 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-08-10 through 2025-08-24
Sun 15:45 Midway, Chicago (MDW) 19:05 Boston Logan (BOS) B
Southwest Airlines WN 483 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-09-07 through 2025-09-28
Sat 15:55 Midway, Chicago (MDW) 19:15 Boston Logan (BOS) B
Southwest Airlines WN 483 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 16:45 Midway, Chicago (MDW) 20:05 Boston Logan (BOS) B
Southwest Airlines WN 483 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-08-07 through 2025-09-29
Sun 19:25 Midway, Chicago (MDW) 22:40 Boston Logan (BOS) B
Southwest Airlines WN 676 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2025-05-25
Sun 20:40 Midway, Chicago (MDW) 23:55 Boston Logan (BOS) B
Southwest Airlines WN 676 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2025-05-18
Sun 20:40 Midway, Chicago (MDW) 23:55 Boston Logan (BOS) B
Southwest Airlines WN 676 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2025-06-01
Mon,Thu,Fri 18:55 Midway, Chicago (MDW) 22:10 Boston Logan (BOS) B
Southwest Airlines WN 937 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 18:55 Midway, Chicago (MDW) 22:10 Boston Logan (BOS) B
Southwest Airlines WN 937 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-07-07 through 2025-08-04
Tue,Wed 19:30 Midway, Chicago (MDW) 22:45 Boston Logan (BOS) B
Southwest Airlines WN 937 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-06-10 through 2025-07-30
Tue,Wed 13:25 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737-700 (73W) 2:20 Effective 2025-06-10 through 2025-07-30
Fri 17:30 Midway, Chicago (MDW) 20:50 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737-800 (73H) 2:20 Operates only on 2025-07-04
Sat 19:00 Midway, Chicago (MDW) 22:15 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri 20:30 Midway, Chicago (MDW) 23:45 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 20:30 Midway, Chicago (MDW) 23:45 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-07-07 through 2025-08-04
Sun 22:00 Midway, Chicago (MDW) 01:15 Boston Logan (BOS) B
Southwest Airlines WN 1011 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-06-08 through 2025-08-03
The flight arrives 1 day after departure.
Sat 18:30 Midway, Chicago (MDW) 21:45 Boston Logan (BOS) B
Southwest Airlines WN 1132 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2025-05-31
Mon,Thu,Fri 19:20 Midway, Chicago (MDW) 22:35 Boston Logan (BOS) B
Southwest Airlines WN 1132 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2025-06-02
Thu 06:55 Midway, Chicago (MDW) 10:10 Boston Logan (BOS) B
Southwest Airlines WN 1148 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2025-11-27
Sun 10:20 Midway, Chicago (MDW) 13:40 Boston Logan (BOS) B
Southwest Airlines WN 1240 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2025-05-18
Sun 10:20 Midway, Chicago (MDW) 13:40 Boston Logan (BOS) B
Southwest Airlines WN 1240 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2025-06-01
Sat 12:10 Midway, Chicago (MDW) 15:30 Boston Logan (BOS) B
Southwest Airlines WN 1240 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2025-05-31
Mon,Thu,Fri 12:30 Midway, Chicago (MDW) 15:50 Boston Logan (BOS) B
Southwest Airlines WN 1240 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2025-06-02
Tue,Wed 13:15 Midway, Chicago (MDW) 16:35 Boston Logan (BOS) B
Southwest Airlines WN 1240 Non-stop Boeing 737-800 (73H) 2:20 Valid until 2025-06-04
Sun 17:50 Midway, Chicago (MDW) 21:05 Boston Logan (BOS) B
Southwest Airlines WN 1402 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2025-11-30
Mon,Thu,Fri 06:00 Midway, Chicago (MDW) 09:15 Boston Logan (BOS) B
Southwest Airlines WN 1427 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-06-05 through 2025-07-03
Sat,Sun 06:00 Midway, Chicago (MDW) 09:15 Boston Logan (BOS) B
Southwest Airlines WN 1427 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-06-07 through 2025-08-03
Mon,Thu,Fri 06:00 Midway, Chicago (MDW) 09:15 Boston Logan (BOS) B
Southwest Airlines WN 1427 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-07-07 through 2025-08-04
Tue,Wed 07:35 Midway, Chicago (MDW) 10:50 Boston Logan (BOS) B
Southwest Airlines WN 1427 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-06-10 through 2025-07-30
Sat 08:20 Midway, Chicago (MDW) 11:40 Boston Logan (BOS) B
Southwest Airlines WN 1497 Non-stop Boeing 737-700 (73W) 2:20 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 09:40 Midway, Chicago (MDW) 13:00 Boston Logan (BOS) B
Southwest Airlines WN 1497 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-08-07 through 2025-09-29
Sun 10:00 Midway, Chicago (MDW) 13:25 Boston Logan (BOS) B
Southwest Airlines WN 1497 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-08-10 through 2025-08-24
Sun 10:00 Midway, Chicago (MDW) 13:25 Boston Logan (BOS) B
Southwest Airlines WN 1497 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-09-07 through 2025-09-28
Sun 10:45 Midway, Chicago (MDW) 14:05 Boston Logan (BOS) B
Southwest Airlines WN 1497 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2025-08-31
Sun 11:55 Midway, Chicago (MDW) 15:10 Boston Logan (BOS) B
Southwest Airlines WN 1544 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-10-05 through 2025-10-26
Sun 21:45 Midway, Chicago (MDW) 01:00 Boston Logan (BOS) B
Southwest Airlines WN 1554 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2025-11-30
The flight arrives 1 day after departure.
Tue,Wed 13:30 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-11-04 through 2025-11-12
Mon-Thu 13:30 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-11-17 through 2025-11-20
Mon-Fri 13:30 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-12-02 through 2025-12-11
Mon-Wed 13:30 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-12-15 through 2025-12-17
Wed,Thu 13:30 Midway, Chicago (MDW) 16:45 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-12-24 through 2026-01-01
Sat 17:35 Midway, Chicago (MDW) 20:50 Boston Logan (BOS) B
Southwest Airlines WN 1773 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2025-11-08 through 2025-11-15
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All airlines flying from Midway, Chicago (MDW) to Boston Logan (BOS).
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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN171
08:00
Midway, Chicago (MDW)

11:15
Boston Logan (BOS) B
Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN171
09:45
Midway, Chicago (MDW)

13:05
Boston Logan (BOS) B
Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN171
10:35
Midway, Chicago (MDW)

13:55
Boston Logan (BOS) B
Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN171
10:35
Midway, Chicago (MDW)

13:55
Boston Logan (BOS) B
Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN278
09:55
Midway, Chicago (MDW)

13:20
Boston Logan (BOS) B
Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN278
12:00
Midway, Chicago (MDW)

15:20
Boston Logan (BOS) B
Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN404
05:30
Midway, Chicago (MDW)

08:45
Boston Logan (BOS) B
Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN404
07:50
Midway, Chicago (MDW)

11:05
Boston Logan (BOS) B
Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN483
15:45
Midway, Chicago (MDW)

19:05
Boston Logan (BOS) B
Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN483
15:45
Midway, Chicago (MDW)

19:05
Boston Logan (BOS) B
Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN483
15:55
Midway, Chicago (MDW)

19:15
Boston Logan (BOS) B
Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN483
16:45
Midway, Chicago (MDW)

20:05
Boston Logan (BOS) B
Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN676
19:25
Midway, Chicago (MDW)

22:40
Boston Logan (BOS) B
Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN676
20:40
Midway, Chicago (MDW)

23:55
Boston Logan (BOS) B
Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN676
20:40
Midway, Chicago (MDW)

23:55
Boston Logan (BOS) B
Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN937
18:55
Midway, Chicago (MDW)

22:10
Boston Logan (BOS) B
Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN937
18:55
Midway, Chicago (MDW)

22:10
Boston Logan (BOS) B
Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN937
19:30
Midway, Chicago (MDW)

22:45
Boston Logan (BOS) B
Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1011
13:25
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN1011
17:30
Midway, Chicago (MDW)

20:50
Boston Logan (BOS) B
Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1011
19:00
Midway, Chicago (MDW)

22:15
Boston Logan (BOS) B
Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1011
20:30
Midway, Chicago (MDW)

23:45
Boston Logan (BOS) B
Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1011
20:30
Midway, Chicago (MDW)

23:45
Boston Logan (BOS) B
Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1011
22:00
Midway, Chicago (MDW)

01:15(+1)
Boston Logan (BOS) B
Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.
Southwest Airlines WN1132
18:30
Midway, Chicago (MDW)

21:45
Boston Logan (BOS) B
Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1132
19:20
Midway, Chicago (MDW)

22:35
Boston Logan (BOS) B
Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1148
06:55
Midway, Chicago (MDW)

10:10
Boston Logan (BOS) B
Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)
Southwest Airlines WN1240
10:20
Midway, Chicago (MDW)

13:40
Boston Logan (BOS) B
Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1240
10:20
Midway, Chicago (MDW)

13:40
Boston Logan (BOS) B
Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1240
12:10
Midway, Chicago (MDW)

15:30
Boston Logan (BOS) B
Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1240
12:30
Midway, Chicago (MDW)

15:50
Boston Logan (BOS) B
Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1240
13:15
Midway, Chicago (MDW)

16:35
Boston Logan (BOS) B
Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1402
17:50
Midway, Chicago (MDW)

21:05
Boston Logan (BOS) B
Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)
Southwest Airlines WN1427
06:00
Midway, Chicago (MDW)

09:15
Boston Logan (BOS) B
Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1427
06:00
Midway, Chicago (MDW)

09:15
Boston Logan (BOS) B
Effective 2025-06-07 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1427
06:00
Midway, Chicago (MDW)

09:15
Boston Logan (BOS) B
Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1427
07:35
Midway, Chicago (MDW)

10:50
Boston Logan (BOS) B
Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1497
08:20
Midway, Chicago (MDW)

11:40
Boston Logan (BOS) B
Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN1497
09:40
Midway, Chicago (MDW)

13:00
Boston Logan (BOS) B
Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1497
10:00
Midway, Chicago (MDW)

13:25
Boston Logan (BOS) B
Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1497
10:00
Midway, Chicago (MDW)

13:25
Boston Logan (BOS) B
Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1497
10:45
Midway, Chicago (MDW)

14:05
Boston Logan (BOS) B
Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1544
11:55
Midway, Chicago (MDW)

15:10
Boston Logan (BOS) B
Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN1554
21:45
Midway, Chicago (MDW)

01:00(+1)
Boston Logan (BOS) B
Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.
Southwest Airlines WN1773
13:30
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1773
13:30
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1773
13:30
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1773
13:30
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1773
13:30
Midway, Chicago (MDW)

16:45
Boston Logan (BOS) B
Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN1773
17:35
Midway, Chicago (MDW)

20:50
Boston Logan (BOS) B
Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)
Ad mobi box here (300x250px) 6815354179 M FlightInfo Bottom Box
Parallax here MDW-BOS
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  • A domestic route departing from the Midway, Chicago airport (MDW) and arriving at Boston Logan airport (BOS).
  • The flight distance is 858 miles, or 1380 km.
  • The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-5 . 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 2:10 and 2:25.
Return (BOS-MDW) flights
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