Southwest Airlines flights from Chicago Midway (MDW) to Boston Logan (BOS).

FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 18:00 Chicago Midway (MDW) 21:20 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-07 through 2026-06-03
Sat 18:05 Chicago Midway (MDW) 21:25 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-04-11 through 2026-05-30
Sun 18:05 Chicago Midway (MDW) 21:25 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-24
Sun 18:45 Chicago Midway (MDW) 22:05 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-12 through 2026-05-17
Sun 18:45 Chicago Midway (MDW) 22:05 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-31
Mon,Thu,Fri 19:00 Chicago Midway (MDW) 22:20 Boston Logan (BOS) B Southwest Airlines WN 2392 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-09 through 2026-06-01
Sat 11:25 Chicago Midway (MDW) 14:45 Boston Logan (BOS) B Southwest Airlines WN 2619 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-11 through 2026-05-30
Tue,Wed 12:45 Chicago Midway (MDW) 16:05 Boston Logan (BOS) B Southwest Airlines WN 2641 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-09 through 2026-07-29
Mon-Fri 14:00 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 14:00 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-01-18 through 2026-01-23
Mon-Fri 14:00 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 14:00 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-02-08 through 2026-02-11
Tue,Wed 14:00 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-02-18 through 2026-03-04
Mon,Thu,Fri 14:15 Chicago Midway (MDW) 17:25 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 14:15 Chicago Midway (MDW) 17:25 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-02-20 through 2026-03-01
Sat 17:40 Chicago Midway (MDW) 20:55 Boston Logan (BOS) B Southwest Airlines WN 2657 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-01-10 through 2026-02-07
Sun 06:00 Chicago Midway (MDW) 09:15 Boston Logan (BOS) B Southwest Airlines WN 2681 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-09 through 2026-09-27
Sat 07:40 Chicago Midway (MDW) 11:00 Boston Logan (BOS) B Southwest Airlines WN 2681 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-08 through 2026-09-26
Mon,Thu,Fri 05:40 Chicago Midway (MDW) 08:55 Boston Logan (BOS) B Southwest Airlines WN 3094 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-08-06 through 2026-09-28
Sun 07:55 Chicago Midway (MDW) 11:25 Boston Logan (BOS) B Southwest Airlines WN 3315 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 08:15 Chicago Midway (MDW) 11:40 Boston Logan (BOS) B Southwest Airlines WN 3315 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-06 through 2026-09-28
Tue,Wed 08:45 Chicago Midway (MDW) 12:15 Boston Logan (BOS) B Southwest Airlines WN 3315 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-04 through 2026-09-30
Sat 09:05 Chicago Midway (MDW) 12:25 Boston Logan (BOS) B Southwest Airlines WN 3315 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-08 through 2026-09-26
Mon,Thu,Fri 11:35 Chicago Midway (MDW) 14:55 Boston Logan (BOS) B Southwest Airlines WN 3329 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-06 through 2026-09-28
Sat 15:10 Chicago Midway (MDW) 18:30 Boston Logan (BOS) B Southwest Airlines WN 3329 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-08 through 2026-09-26
Sun 16:15 Chicago Midway (MDW) 19:35 Boston Logan (BOS) B Southwest Airlines WN 3329 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-09 through 2026-09-27
Sat 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 3352 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-07 through 2026-04-04
Sun 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 3352 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 07:55 Chicago Midway (MDW) 11:10 Boston Logan (BOS) B Southwest Airlines WN 3352 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-05 through 2026-04-06
Tue,Wed 08:00 Chicago Midway (MDW) 11:20 Boston Logan (BOS) B Southwest Airlines WN 3352 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-10 through 2026-04-01
Sat 12:00 Chicago Midway (MDW) 15:20 Boston Logan (BOS) B Southwest Airlines WN 3456 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-06 through 2026-08-01
Sun 18:45 Chicago Midway (MDW) 22:00 Boston Logan (BOS) B Southwest Airlines WN 3521 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-07 through 2026-08-02
Sun 19:30 Chicago Midway (MDW) 22:45 Boston Logan (BOS) B Southwest Airlines WN 3587 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-08 through 2026-04-05
Mon,Tue,Fri,Sun 09:35 Chicago Midway (MDW) 12:50 Boston Logan (BOS) B Southwest Airlines WN 3678 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-05
Sat 09:50 Chicago Midway (MDW) 13:10 Boston Logan (BOS) B Southwest Airlines WN 3678 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2026-01-03
Wed,Thu 18:15 Chicago Midway (MDW) 21:35 Boston Logan (BOS) B Southwest Airlines WN 3678 Non-stop Boeing 737-800 (73H) 2:20 Valid until 2026-01-01
Mon 14:25 Chicago Midway (MDW) 17:40 Boston Logan (BOS) B Southwest Airlines WN 3680 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-01-05
Sat 15:10 Chicago Midway (MDW) 18:25 Boston Logan (BOS) B Southwest Airlines WN 3680 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2026-01-03
Mon,Tue,Fri,Sun 16:05 Chicago Midway (MDW) 19:20 Boston Logan (BOS) B Southwest Airlines WN 3680 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-04
Mon,Thu,Fri 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 3737 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-09 through 2026-06-01
Sun 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 3737 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 3737 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-05-31
Tue,Wed 12:45 Chicago Midway (MDW) 16:05 Boston Logan (BOS) B Southwest Airlines WN 3737 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 13:55 Chicago Midway (MDW) 17:20 Boston Logan (BOS) B Southwest Airlines WN 4215 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-06 through 2026-09-28
Sun 17:55 Chicago Midway (MDW) 21:20 Boston Logan (BOS) B Southwest Airlines WN 4215 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-09 through 2026-09-27
Tue,Wed 18:00 Chicago Midway (MDW) 21:20 Boston Logan (BOS) B Southwest Airlines WN 4215 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-04 through 2026-09-30
Sun 05:15 Chicago Midway (MDW) 08:25 Boston Logan (BOS) B Southwest Airlines WN 4611 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-06-07 through 2026-08-02
Sat 05:25 Chicago Midway (MDW) 08:40 Boston Logan (BOS) B Southwest Airlines WN 4611 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 4611 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Tue,Wed 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 4611 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-09 through 2026-07-29

1 2 3

A domestic route departing from the Chicago Midway 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 2:30.

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Southwest Airlines flights from Chicago Midway (MDW) to Boston Logan (BOS).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN2392

18:00

Chicago Midway (MDW)

21:20

Boston Logan (BOS) B

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2392

18:05

Chicago Midway (MDW)

21:25

Boston Logan (BOS) B

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2392

18:05

Chicago Midway (MDW)

21:25

Boston Logan (BOS) B

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2392

18:45

Chicago Midway (MDW)

22:05

Boston Logan (BOS) B

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2392

18:45

Chicago Midway (MDW)

22:05

Boston Logan (BOS) B

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2392

19:00

Chicago Midway (MDW)

22:20

Boston Logan (BOS) B

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2619

11:25

Chicago Midway (MDW)

14:45

Boston Logan (BOS) B

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2641

12:45

Chicago Midway (MDW)

16:05

Boston Logan (BOS) B

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2657

14:00

Chicago Midway (MDW)

17:10

Boston Logan (BOS) B

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2657

14:00

Chicago Midway (MDW)

17:10

Boston Logan (BOS) B

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2657

14:00

Chicago Midway (MDW)

17:10

Boston Logan (BOS) B

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2657

14:00

Chicago Midway (MDW)

17:10

Boston Logan (BOS) B

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2657

14:00

Chicago Midway (MDW)

17:10

Boston Logan (BOS) B

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2657

14:15

Chicago Midway (MDW)

17:25

Boston Logan (BOS) B

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2657

14:15

Chicago Midway (MDW)

17:25

Boston Logan (BOS) B

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2657

17:40

Chicago Midway (MDW)

20:55

Boston Logan (BOS) B

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2681

06:00

Chicago Midway (MDW)

09:15

Boston Logan (BOS) B

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2681

07:40

Chicago Midway (MDW)

11:00

Boston Logan (BOS) B

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3094

05:40

Chicago Midway (MDW)

08:55

Boston Logan (BOS) B

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3315

07:55

Chicago Midway (MDW)

11:25

Boston Logan (BOS) B

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3315

08:15

Chicago Midway (MDW)

11:40

Boston Logan (BOS) B

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3315

08:45

Chicago Midway (MDW)

12:15

Boston Logan (BOS) B

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3315

09:05

Chicago Midway (MDW)

12:25

Boston Logan (BOS) B

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3329

11:35

Chicago Midway (MDW)

14:55

Boston Logan (BOS) B

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3329

15:10

Chicago Midway (MDW)

18:30

Boston Logan (BOS) B

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3329

16:15

Chicago Midway (MDW)

19:35

Boston Logan (BOS) B

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3352

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3352

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3352

07:55

Chicago Midway (MDW)

11:10

Boston Logan (BOS) B

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3352

08:00

Chicago Midway (MDW)

11:20

Boston Logan (BOS) B

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3456

12:00

Chicago Midway (MDW)

15:20

Boston Logan (BOS) B

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3521

18:45

Chicago Midway (MDW)

22:00

Boston Logan (BOS) B

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3587

19:30

Chicago Midway (MDW)

22:45

Boston Logan (BOS) B

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3678

09:35

Chicago Midway (MDW)

12:50

Boston Logan (BOS) B

Valid until 2026-01-05

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3678

09:50

Chicago Midway (MDW)

13:10

Boston Logan (BOS) B

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3678

18:15

Chicago Midway (MDW)

21:35

Boston Logan (BOS) B

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3680

14:25

Chicago Midway (MDW)

17:40

Boston Logan (BOS) B

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3680

15:10

Chicago Midway (MDW)

18:25

Boston Logan (BOS) B

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3680

16:05

Chicago Midway (MDW)

19:20

Boston Logan (BOS) B

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3737

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3737

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3737

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3737

12:45

Chicago Midway (MDW)

16:05

Boston Logan (BOS) B

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4215

13:55

Chicago Midway (MDW)

17:20

Boston Logan (BOS) B

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4215

17:55

Chicago Midway (MDW)

21:20

Boston Logan (BOS) B

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4215

18:00

Chicago Midway (MDW)

21:20

Boston Logan (BOS) B

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4611

05:15

Chicago Midway (MDW)

08:25

Boston Logan (BOS) B

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4611

05:25

Chicago Midway (MDW)

08:40

Boston Logan (BOS) B

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4611

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4611

07:40

Chicago Midway (MDW)

10:55

Boston Logan (BOS) B

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

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A domestic route departing from the Chicago Midway 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 2:30.

All MDW-BOS flights

All Southwest Airlines flights

Return (BOS-MDW) flights

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