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

FLIGHT SCHEDULE
Direct Flights:
Sat 18:10 Chicago Midway (MDW) 21:25 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-14 through 2026-02-28
Thu,Fri,Sun 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-01-11 through 2026-01-16
Mon,Sun 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-01 through 2026-02-06
Mon,Sun 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-17 through 2026-02-23
Mon 18:35 Chicago Midway (MDW) 21:50 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-03-02
Mon,Thu,Fri 19:40 Chicago Midway (MDW) 22:55 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 19:40 Chicago Midway (MDW) 22:55 Boston Logan (BOS) B Southwest Airlines WN 4806 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-02-20 through 2026-03-01
Mon,Tue,Fri,Sun 05:30 Chicago Midway (MDW) 08:45 Boston Logan (BOS) B Southwest Airlines WN 4825 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-04
Sat 06:00 Chicago Midway (MDW) 09:15 Boston Logan (BOS) B Southwest Airlines WN 4825 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-03
Sat 11:20 Chicago Midway (MDW) 14:40 Boston Logan (BOS) B Southwest Airlines WN 4860 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-08 through 2026-09-26
Tue,Wed 12:40 Chicago Midway (MDW) 16:00 Boston Logan (BOS) B Southwest Airlines WN 4860 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 18:25 Chicago Midway (MDW) 21:45 Boston Logan (BOS) B Southwest Airlines WN 4860 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-06 through 2026-09-28
Sun 13:45 Chicago Midway (MDW) 17:05 Boston Logan (BOS) B Southwest Airlines WN 4975 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-06-07 through 2026-08-02
Tue,Wed 14:30 Chicago Midway (MDW) 17:50 Boston Logan (BOS) B Southwest Airlines WN 4975 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 16:00 Chicago Midway (MDW) 19:20 Boston Logan (BOS) B Southwest Airlines WN 4975 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-04 through 2026-08-03
Sat 17:45 Chicago Midway (MDW) 21:05 Boston Logan (BOS) B Southwest Airlines WN 4975 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-06-06 through 2026-08-01
Non-Direct Flights:
Fri,Sun 13:20 Chicago Midway (MDW) 18:15 Boston Logan (BOS) B Southwest Airlines WN 2120 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-01-02 through 2026-01-04
Mon,Thu,Fri 12:50 Chicago Midway (MDW) 20:05 Boston Logan (BOS) B Southwest Airlines WN 3403 2-stop Boeing 737-700 (Scimitar Winglets) 6:15 Effective 2026-04-09 through 2026-06-01

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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.

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN4806

18:10

Chicago Midway (MDW)

21:25

Boston Logan (BOS) B

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4806

18:35

Chicago Midway (MDW)

21:50

Boston Logan (BOS) B

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4806

19:40

Chicago Midway (MDW)

22:55

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4806

19:40

Chicago Midway (MDW)

22:55

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4825

05:30

Chicago Midway (MDW)

08:45

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 WN4825

06:00

Chicago Midway (MDW)

09:15

Boston Logan (BOS) B

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN4860

11:20

Chicago Midway (MDW)

14:40

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 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4860

12:40

Chicago Midway (MDW)

16:00

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 737-800 (73H)

Direct Flights:

Southwest Airlines WN4860

18:25

Chicago Midway (MDW)

21:45

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 WN4975

13:45

Chicago Midway (MDW)

17:05

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 737-800 (73H)

Direct Flights:

Southwest Airlines WN4975

14:30

Chicago Midway (MDW)

17:50

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 WN4975

16:00

Chicago Midway (MDW)

19:20

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 WN4975

17:45

Chicago Midway (MDW)

21:05

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 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2120

13:20

Chicago Midway (MDW)

18:15

Boston Logan (BOS) B

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3403

12:50

Chicago Midway (MDW)

20:05

Boston Logan (BOS) B

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 2-stop
Boeing 737-700 (Scimitar Winglets)

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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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