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

FLIGHT SCHEDULE
Direct Flights:
Sat 15:30 Boston Logan (BOS) B 17:15 Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-04-11 through 2026-05-30
Tue,Wed 18:20 Boston Logan (BOS) B 20:10 Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 18:55 Boston Logan (BOS) B 20:45 Chicago Midway (MDW) Southwest Airlines WN 3665 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-09 through 2026-06-01
Mon,Tue,Fri,Sun 09:25 Boston Logan (BOS) B 11:15 Chicago Midway (MDW) Southwest Airlines WN 3724 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04
Sat 19:55 Boston Logan (BOS) B 21:40 Chicago Midway (MDW) Southwest Airlines WN 3725 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Operates only on 2026-01-03
Sun 17:40 Boston Logan (BOS) B 19:20 Chicago Midway (MDW) Southwest Airlines WN 3738 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-08-09 through 2026-09-27
Sat 10:25 Boston Logan (BOS) B 12:10 Chicago Midway (MDW) Southwest Airlines WN 3771 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2026-01-03
Tue,Wed 17:30 Boston Logan (BOS) B 19:20 Chicago Midway (MDW) Southwest Airlines WN 3911 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-06-09 through 2026-07-29
Sat 17:45 Boston Logan (BOS) B 19:35 Chicago Midway (MDW) Southwest Airlines WN 3911 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 18:45 Boston Logan (BOS) B 20:35 Chicago Midway (MDW) Southwest Airlines WN 3911 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-04 through 2026-08-03
Tue,Wed 15:45 Boston Logan (BOS) B 17:30 Chicago Midway (MDW) Southwest Airlines WN 4106 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 16:45 Boston Logan (BOS) B 18:35 Chicago Midway (MDW) Southwest Airlines WN 4106 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-04 through 2026-08-03
Sat 13:00 Boston Logan (BOS) B 14:35 Chicago Midway (MDW) Southwest Airlines WN 4298 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-08 through 2026-09-26
Sun 17:50 Boston Logan (BOS) B 19:35 Chicago Midway (MDW) Southwest Airlines WN 4618 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Operates only on 2026-05-24
Sun 18:50 Boston Logan (BOS) B 20:40 Chicago Midway (MDW) Southwest Airlines WN 4618 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-12 through 2026-05-17
Sun 18:50 Boston Logan (BOS) B 20:40 Chicago Midway (MDW) Southwest Airlines WN 4618 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-05-31
Sun 14:10 Boston Logan (BOS) B 15:45 Chicago Midway (MDW) Southwest Airlines WN 4657 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-08-09 through 2026-09-27
Non-Direct Flights:
Wed,Thu 17:35 Boston Logan (BOS) B 21:05 Chicago Midway (MDW) Southwest Airlines WN 487 1-stop Boeing 737-800 (73H) 4:30 Valid until 2026-01-01
Sun 08:10 Boston Logan (BOS) B 12:20 Chicago Midway (MDW) Southwest Airlines WN 3397 1-stop Boeing 737-700 (Scimitar Winglets) 5:10 Effective 2026-03-08 through 2026-04-05
Mon 13:25 Boston Logan (BOS) B 19:05 Chicago Midway (MDW) Southwest Airlines WN 1419 2-stop Boeing 737-700 (Scimitar Winglets) 6:40 Operates only on 2026-01-05
Sun 08:15 Boston Logan (BOS) B 17:40 Chicago Midway (MDW) Southwest Airlines WN 2743 3-stop Boeing 737-700 (Scimitar Winglets) 10:25 Effective 2026-04-12 through 2026-05-17
Sun 08:15 Boston Logan (BOS) B 17:40 Chicago Midway (MDW) Southwest Airlines WN 2743 3-stop Boeing 737-700 (Scimitar Winglets) 10:25 Operates only on 2026-05-31

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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.

Return (MDW-BOS) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN3665

15:30

Boston Logan (BOS) B

17:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3665

18:20

Boston Logan (BOS) B

20:10

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3665

18:55

Boston Logan (BOS) B

20:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3724

09:25

Boston Logan (BOS) B

11:15

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3725

19:55

Boston Logan (BOS) B

21:40

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3738

17:40

Boston Logan (BOS) B

19:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3771

10:25

Boston Logan (BOS) B

12:10

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3911

17:30

Boston Logan (BOS) B

19:20

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3911

17:45

Boston Logan (BOS) B

19:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3911

18:45

Boston Logan (BOS) B

20:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4106

15:45

Boston Logan (BOS) B

17:30

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4106

16:45

Boston Logan (BOS) B

18:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4298

13:00

Boston Logan (BOS) B

14:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4618

17:50

Boston Logan (BOS) B

19:35

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4618

18:50

Boston Logan (BOS) B

20:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4618

18:50

Boston Logan (BOS) B

20:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4657

14:10

Boston Logan (BOS) B

15:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN487

17:35

Boston Logan (BOS) B

21:05

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:30, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3397

08:10

Boston Logan (BOS) B

12:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1419

13:25

Boston Logan (BOS) B

19:05

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2743

08:15

Boston Logan (BOS) B

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:25, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2743

08:15

Boston Logan (BOS) B

17:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:25, 3-stop
Boeing 737-700 (Scimitar Winglets)

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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.

Return (MDW-BOS) flights

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