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

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 09:25 Chicago Midway (MDW) 12:40 Boston Logan (BOS) B Southwest Airlines WN 164 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-09 through 2026-06-01
Mon,Thu,Fri 19:35 Chicago Midway (MDW) 22:50 Boston Logan (BOS) B Southwest Airlines WN 232 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Sat 08:15 Chicago Midway (MDW) 11:30 Boston Logan (BOS) B Southwest Airlines WN 356 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-06 through 2026-08-01
Tue,Wed 12:10 Chicago Midway (MDW) 15:20 Boston Logan (BOS) B Southwest Airlines WN 493 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-03-10 through 2026-04-01
Tue 06:40 Chicago Midway (MDW) 09:55 Boston Logan (BOS) B Southwest Airlines WN 547 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-08-04 through 2026-09-29
Wed 06:40 Chicago Midway (MDW) 09:55 Boston Logan (BOS) B Southwest Airlines WN 553 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-08-05 through 2026-09-30
Mon,Thu,Fri 06:05 Chicago Midway (MDW) 09:25 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 06:05 Chicago Midway (MDW) 09:25 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-20 through 2026-03-01
Thu,Fri,Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-11 through 2026-01-16
Mon,Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-01 through 2026-02-06
Mon,Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-17 through 2026-02-23
Mon 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-03-02
Sat 10:15 Chicago Midway (MDW) 13:30 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-01-10 through 2026-02-28
Mon-Fri 17:35 Chicago Midway (MDW) 20:50 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 17:35 Chicago Midway (MDW) 20:50 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-18 through 2026-01-23
Mon-Fri 17:35 Chicago Midway (MDW) 20:50 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 17:35 Chicago Midway (MDW) 20:50 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-08 through 2026-02-11
Tue,Wed 17:35 Chicago Midway (MDW) 20:50 Boston Logan (BOS) B Southwest Airlines WN 987 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-18 through 2026-03-04
Sun 12:05 Chicago Midway (MDW) 15:25 Boston Logan (BOS) B Southwest Airlines WN 1057 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-09 through 2026-09-27
Sun 12:45 Chicago Midway (MDW) 16:05 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-24
Mon,Thu,Fri 13:55 Chicago Midway (MDW) 17:10 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-09 through 2026-06-01
Sun 14:05 Chicago Midway (MDW) 17:20 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 14:05 Chicago Midway (MDW) 17:20 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-05-31
Tue,Wed 15:15 Chicago Midway (MDW) 18:35 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-07 through 2026-06-03
Sat 15:30 Chicago Midway (MDW) 18:45 Boston Logan (BOS) B Southwest Airlines WN 1280 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-11 through 2026-05-30
Tue,Wed 18:05 Chicago Midway (MDW) 21:20 Boston Logan (BOS) B Southwest Airlines WN 1374 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-09 through 2026-07-29
Sun 07:40 Chicago Midway (MDW) 10:55 Boston Logan (BOS) B Southwest Airlines WN 1405 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Tue,Wed 09:00 Chicago Midway (MDW) 12:15 Boston Logan (BOS) B Southwest Airlines WN 1405 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 09:20 Chicago Midway (MDW) 12:40 Boston Logan (BOS) B Southwest Airlines WN 1405 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-04 through 2026-08-03
Sun 12:10 Chicago Midway (MDW) 15:30 Boston Logan (BOS) B Southwest Airlines WN 1498 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 13:20 Chicago Midway (MDW) 16:30 Boston Logan (BOS) B Southwest Airlines WN 1716 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-03-05 through 2026-04-06
Sun 13:40 Chicago Midway (MDW) 16:50 Boston Logan (BOS) B Southwest Airlines WN 1716 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-03-08 through 2026-04-05
Tue,Wed 14:35 Chicago Midway (MDW) 17:45 Boston Logan (BOS) B Southwest Airlines WN 1740 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-03-10 through 2026-04-01
Sat 14:45 Chicago Midway (MDW) 18:00 Boston Logan (BOS) B Southwest Airlines WN 1740 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 15:30 Chicago Midway (MDW) 18:45 Boston Logan (BOS) B Southwest Airlines WN 1740 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-05 through 2026-04-06
Sun 15:45 Chicago Midway (MDW) 19:00 Boston Logan (BOS) B Southwest Airlines WN 1740 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-08 through 2026-04-05
Wed,Thu 13:30 Chicago Midway (MDW) 16:45 Boston Logan (BOS) B Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2026-01-01
Mon 19:15 Chicago Midway (MDW) 22:30 Boston Logan (BOS) B Southwest Airlines WN 1773 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-01-05
Fri,Sun 19:50 Chicago Midway (MDW) 23:05 Boston Logan (BOS) B Southwest Airlines WN 1773 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-01-02 through 2026-01-04
Sat 20:40 Chicago Midway (MDW) 23:55 Boston Logan (BOS) B Southwest Airlines WN 1773 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2026-01-03
Tue,Wed,Sat 07:45 Chicago Midway (MDW) 11:00 Boston Logan (BOS) B Southwest Airlines WN 1800 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-07 through 2026-06-03
Sun 08:50 Chicago Midway (MDW) 12:10 Boston Logan (BOS) B Southwest Airlines WN 1800 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-24
Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 1800 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 09:40 Chicago Midway (MDW) 12:55 Boston Logan (BOS) B Southwest Airlines WN 1800 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-05-31
Tue,Wed 18:10 Chicago Midway (MDW) 21:25 Boston Logan (BOS) B Southwest Airlines WN 1930 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-10 through 2026-04-01
Sat 18:45 Chicago Midway (MDW) 22:00 Boston Logan (BOS) B Southwest Airlines WN 1930 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 19:00 Chicago Midway (MDW) 22:15 Boston Logan (BOS) B Southwest Airlines WN 1930 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-05 through 2026-04-06
Mon,Thu,Fri 12:25 Chicago Midway (MDW) 15:45 Boston Logan (BOS) B Southwest Airlines WN 2270 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-04 through 2026-08-03

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.

Return (BOS-MDW) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN164

09:25

Chicago Midway (MDW)

12:40

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN232

19:35

Chicago Midway (MDW)

22:50

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 WN356

08:15

Chicago Midway (MDW)

11:30

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 WN493

12:10

Chicago Midway (MDW)

15:20

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN547

06:40

Chicago Midway (MDW)

09:55

Boston Logan (BOS) B

Effective 2026-08-04 through 2026-09-29

Mon
-

Tue

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN553

06:40

Chicago Midway (MDW)

09:55

Boston Logan (BOS) B

Effective 2026-08-05 through 2026-09-30

Mon
-

Tue
-

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

06:05

Chicago Midway (MDW)

09:25

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

06:05

Chicago Midway (MDW)

09:25

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

09:40

Chicago Midway (MDW)

12:55

Boston Logan (BOS) B

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

10:15

Chicago Midway (MDW)

13:30

Boston Logan (BOS) B

Effective 2026-01-10 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN987

17:35

Chicago Midway (MDW)

20:50

Boston Logan (BOS) B

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

17:35

Chicago Midway (MDW)

20:50

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

17:35

Chicago Midway (MDW)

20:50

Boston Logan (BOS) B

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN987

17:35

Chicago Midway (MDW)

20:50

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN987

17:35

Chicago Midway (MDW)

20:50

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1057

12:05

Chicago Midway (MDW)

15:25

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 WN1280

12:45

Chicago Midway (MDW)

16:05

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 WN1280

13:55

Chicago Midway (MDW)

17:10

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1280

14:05

Chicago Midway (MDW)

17:20

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 WN1280

14:05

Chicago Midway (MDW)

17:20

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 WN1280

15:15

Chicago Midway (MDW)

18:35

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 WN1280

15:30

Chicago Midway (MDW)

18:45

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1374

18:05

Chicago Midway (MDW)

21:20

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1405

07:40

Chicago Midway (MDW)

10:55

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1405

09:00

Chicago Midway (MDW)

12:15

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1405

09:20

Chicago Midway (MDW)

12:40

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1498

12:10

Chicago Midway (MDW)

15:30

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1716

13:20

Chicago Midway (MDW)

16:30

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1716

13:40

Chicago Midway (MDW)

16:50

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1740

14:35

Chicago Midway (MDW)

17:45

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1740

14:45

Chicago Midway (MDW)

18:00

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1740

15:30

Chicago Midway (MDW)

18:45

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1740

15:45

Chicago Midway (MDW)

19:00

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 WN1773

13:30

Chicago Midway (MDW)

16:45

Boston Logan (BOS) B

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1773

19:15

Chicago Midway (MDW)

22:30

Boston Logan (BOS) B

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1773

19:50

Chicago Midway (MDW)

23:05

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1773

20:40

Chicago Midway (MDW)

23:55

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 WN1800

07:45

Chicago Midway (MDW)

11:00

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1800

08:50

Chicago Midway (MDW)

12:10

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 WN1800

09:40

Chicago Midway (MDW)

12:55

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 WN1800

09:40

Chicago Midway (MDW)

12:55

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 WN1930

18:10

Chicago Midway (MDW)

21:25

Boston Logan (BOS) B

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1930

18:45

Chicago Midway (MDW)

22:00

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1930

19:00

Chicago Midway (MDW)

22:15

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2270

12:25

Chicago Midway (MDW)

15:45

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, 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.

Return (BOS-MDW) flights

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