All airlines flying from Jacksonville (JAX) to Midway, Chicago (MDW).

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FLIGHT SCHEDULE
Direct Flights:
Mon-Wed 19:35 Jacksonville (JAX) 21:05 Midway, Chicago (MDW) Southwest Airlines WN 582 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 19:35 Jacksonville (JAX) 21:05 Midway, Chicago (MDW) Southwest Airlines WN 582 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2025-12-19 through 2026-01-04
Sat 20:20 Jacksonville (JAX) 21:45 Midway, Chicago (MDW) Southwest Airlines WN 582 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-22 through 2025-11-29
Sat 20:20 Jacksonville (JAX) 21:45 Midway, Chicago (MDW) Southwest Airlines WN 582 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-20 through 2026-01-03
Sun 15:05 Jacksonville (JAX) 16:35 Midway, Chicago (MDW) Southwest Airlines WN 801 Non-stop Boeing 737-800 (73H) 2:30 Operates only on 2025-05-25
Sun 15:20 Jacksonville (JAX) 16:50 Midway, Chicago (MDW) Southwest Airlines WN 801 Non-stop Boeing 737-700 (73W) 2:30 Valid until 2025-05-18
Sun 15:20 Jacksonville (JAX) 16:50 Midway, Chicago (MDW) Southwest Airlines WN 801 Non-stop Boeing 737-700 (73W) 2:30 Operates only on 2025-06-01
Mon,Thu,Fri,Sun 15:50 Jacksonville (JAX) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 15:50 Jacksonville (JAX) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-21 through 2025-11-28
Fri,Sun 15:50 Jacksonville (JAX) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-07 through 2025-12-14
Thu 15:50 Jacksonville (JAX) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2025-12-18
Mon 15:50 Jacksonville (JAX) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-05
Tue,Wed 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-04 through 2025-11-12
Mon-Thu 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-17 through 2025-11-20
Mon-Fri 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-02 through 2025-12-11
Mon-Wed 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-15 through 2025-12-17
Wed,Thu 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-24 through 2026-01-01
Sun 20:15 Jacksonville (JAX) 21:40 Midway, Chicago (MDW) Southwest Airlines WN 1008 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2025-11-30
Sat 05:35 Jacksonville (JAX) 07:00 Midway, Chicago (MDW) Southwest Airlines WN 1324 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-08 through 2025-11-15
Sat 05:35 Jacksonville (JAX) 07:00 Midway, Chicago (MDW) Southwest Airlines WN 1324 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-06 through 2025-12-13
Sat 14:20 Jacksonville (JAX) 15:45 Midway, Chicago (MDW) Southwest Airlines WN 2476 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-10-04 through 2025-11-01
Tue,Wed 14:50 Jacksonville (JAX) 16:10 Midway, Chicago (MDW) Southwest Airlines WN 2476 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri 15:55 Jacksonville (JAX) 17:20 Midway, Chicago (MDW) Southwest Airlines WN 2476 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-10-02 through 2025-10-31
Sun 17:15 Jacksonville (JAX) 18:40 Midway, Chicago (MDW) Southwest Airlines WN 2476 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-10-05 through 2025-10-26
Sun 10:55 Jacksonville (JAX) 12:20 Midway, Chicago (MDW) Southwest Airlines WN 2735 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-06-08 through 2025-08-03
Tue,Wed 13:20 Jacksonville (JAX) 14:45 Midway, Chicago (MDW) Southwest Airlines WN 3097 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-08-05 through 2025-10-01
Sat 14:05 Jacksonville (JAX) 15:30 Midway, Chicago (MDW) Southwest Airlines WN 3097 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-09 through 2025-09-27
Sun 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 3097 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-08-10 through 2025-08-24
Sun 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 3097 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-09-07 through 2025-09-28
Mon,Thu,Fri 18:05 Jacksonville (JAX) 19:30 Midway, Chicago (MDW) Southwest Airlines WN 3097 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-07 through 2025-09-29
Tue,Wed 16:20 Jacksonville (JAX) 17:45 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-06-10 through 2025-07-30
Fri 17:00 Jacksonville (JAX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2025-07-04
Mon,Thu,Fri 17:25 Jacksonville (JAX) 18:50 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 17:25 Jacksonville (JAX) 18:50 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-07-07 through 2025-08-04
Sat 19:25 Jacksonville (JAX) 20:55 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-800 (73H) 2:30 Effective 2025-06-07 through 2025-08-02
Sun 19:35 Jacksonville (JAX) 21:00 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-06-08 through 2025-08-03
Tue,Wed 07:25 Jacksonville (JAX) 08:55 Midway, Chicago (MDW) Southwest Airlines WN 3851 Non-stop Boeing 737-700 (73W) 2:30 Valid until 2025-06-04
Sat 17:25 Jacksonville (JAX) 19:05 Midway, Chicago (MDW) Southwest Airlines WN 3851 Non-stop Boeing 737-800 (73H) 2:40 Valid until 2025-05-31
Mon,Thu,Fri 17:45 Jacksonville (JAX) 19:20 Midway, Chicago (MDW) Southwest Airlines WN 3851 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Valid until 2025-06-02
Sat 05:35 Jacksonville (JAX) 07:00 Midway, Chicago (MDW) Southwest Airlines WN 4290 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-06-07 through 2025-08-02
Sun 06:40 Jacksonville (JAX) 08:10 Midway, Chicago (MDW) Southwest Airlines WN 4679 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Operates only on 2025-11-30
Non-Direct Flights:
Sun 16:40 Jacksonville (JAX) 20:30 Midway, Chicago (MDW) Southwest Airlines WN 1987 1-stop Boeing 737-800 (73H) 4:50 Operates only on 2025-11-30
Sun 10:50 Jacksonville (JAX) 14:15 Midway, Chicago (MDW) Southwest Airlines WN 2158 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2025-10-05 through 2025-10-26
Tue,Wed 11:50 Jacksonville (JAX) 17:35 Midway, Chicago (MDW) Southwest Airlines WN 1173 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 11:50 Jacksonville (JAX) 17:35 Midway, Chicago (MDW) Southwest Airlines WN 1173 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2025-11-17 through 2025-11-20
Mon-Fri 11:50 Jacksonville (JAX) 17:35 Midway, Chicago (MDW) Southwest Airlines WN 1173 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2025-12-02 through 2025-12-11
Mon-Wed 11:50 Jacksonville (JAX) 17:35 Midway, Chicago (MDW) Southwest Airlines WN 1173 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2025-12-15 through 2025-12-17
Wed,Thu 11:50 Jacksonville (JAX) 17:35 Midway, Chicago (MDW) Southwest Airlines WN 1173 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2025-12-24 through 2026-01-01
Sat 07:45 Jacksonville (JAX) 12:20 Midway, Chicago (MDW) Southwest Airlines WN 2593 2-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2025-10-04 through 2025-11-01

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Parallax here JAX-MDW

A domestic route departing from the Jacksonville airport (JAX) and arriving at Midway, Chicago airport (MDW).
The flight distance is 849 miles, or 1367 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 2:20 and 2:40.

Return (MDW-JAX) flights

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All airlines flying from Jacksonville (JAX) to Midway, Chicago (MDW).

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN582

19:35

Jacksonville (JAX)

21:05

Midway, Chicago (MDW)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN582

19:35

Jacksonville (JAX)

21:05

Midway, Chicago (MDW)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN582

20:20

Jacksonville (JAX)

21:45

Midway, Chicago (MDW)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN582

20:20

Jacksonville (JAX)

21:45

Midway, Chicago (MDW)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN801

15:05

Jacksonville (JAX)

16:35

Midway, Chicago (MDW)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN801

15:20

Jacksonville (JAX)

16:50

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN801

15:20

Jacksonville (JAX)

16:50

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1008

15:50

Jacksonville (JAX)

17:15

Midway, Chicago (MDW)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1008

15:50

Jacksonville (JAX)

17:15

Midway, Chicago (MDW)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1008

15:50

Jacksonville (JAX)

17:15

Midway, Chicago (MDW)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1008

15:50

Jacksonville (JAX)

17:15

Midway, Chicago (MDW)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1008

15:50

Jacksonville (JAX)

17:15

Midway, Chicago (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1008

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1008

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1008

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1008

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1008

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1008

20:15

Jacksonville (JAX)

21:40

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1324

05:35

Jacksonville (JAX)

07:00

Midway, Chicago (MDW)

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1324

05:35

Jacksonville (JAX)

07:00

Midway, Chicago (MDW)

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2476

14:20

Jacksonville (JAX)

15:45

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2476

14:50

Jacksonville (JAX)

16:10

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2476

15:55

Jacksonville (JAX)

17:20

Midway, Chicago (MDW)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2476

17:15

Jacksonville (JAX)

18:40

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2735

10:55

Jacksonville (JAX)

12:20

Midway, Chicago (MDW)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN3097

13:20

Jacksonville (JAX)

14:45

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3097

14:05

Jacksonville (JAX)

15:30

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3097

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

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 WN3097

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

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 WN3097

18:05

Jacksonville (JAX)

19:30

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3234

16:20

Jacksonville (JAX)

17:45

Midway, Chicago (MDW)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3234

17:00

Jacksonville (JAX)

18:25

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN3234

17:25

Jacksonville (JAX)

18:50

Midway, Chicago (MDW)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN3234

17:25

Jacksonville (JAX)

18:50

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN3234

19:25

Jacksonville (JAX)

20:55

Midway, Chicago (MDW)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN3234

19:35

Jacksonville (JAX)

21:00

Midway, Chicago (MDW)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3851

07:25

Jacksonville (JAX)

08:55

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3851

17:25

Jacksonville (JAX)

19:05

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN3851

17:45

Jacksonville (JAX)

19:20

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN4290

05:35

Jacksonville (JAX)

07:00

Midway, Chicago (MDW)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4679

06:40

Jacksonville (JAX)

08:10

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1987

16:40

Jacksonville (JAX)

20:30

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:50, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN2158

10:50

Jacksonville (JAX)

14:15

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1173

11:50

Jacksonville (JAX)

17:35

Midway, Chicago (MDW)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1173

11:50

Jacksonville (JAX)

17:35

Midway, Chicago (MDW)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1173

11:50

Jacksonville (JAX)

17:35

Midway, Chicago (MDW)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1173

11:50

Jacksonville (JAX)

17:35

Midway, Chicago (MDW)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1173

11:50

Jacksonville (JAX)

17:35

Midway, Chicago (MDW)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2593

07:45

Jacksonville (JAX)

12:20

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:35, 2-stop
Boeing 737-700 (Scimitar Winglets)

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Parallax here JAX-MDW

A domestic route departing from the Jacksonville airport (JAX) and arriving at Midway, Chicago airport (MDW).
The flight distance is 849 miles, or 1367 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 2:20 and 2:40.

Return (MDW-JAX) flights

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