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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 13:40 Chicago Midway (MDW) 16:55 Jacksonville (JAX)
Southwest Airlines WN 444 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-09 through 2026-09-27
Sat 11:40 Chicago Midway (MDW) 14:55 Jacksonville (JAX)
Southwest Airlines WN 493 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-07 through 2026-04-04
Tue,Wed 12:50 Chicago Midway (MDW) 16:10 Jacksonville (JAX)
Southwest Airlines WN 1780 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-09 through 2026-07-29
Tue,Wed 18:00 Chicago Midway (MDW) 21:15 Jacksonville (JAX)
Southwest Airlines WN 1864 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 1864 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-05 through 2026-04-06
Sun 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 1864 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-08 through 2026-04-05
Sat 19:00 Chicago Midway (MDW) 22:15 Jacksonville (JAX)
Southwest Airlines WN 1864 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-07 through 2026-04-04
Sat 15:45 Chicago Midway (MDW) 19:00 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-04-11 through 2026-05-30
Tue,Wed 17:55 Chicago Midway (MDW) 21:10 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-09 through 2026-06-01
Sun 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-05-31
Sun 19:50 Chicago Midway (MDW) 23:05 Jacksonville (JAX)
Southwest Airlines WN 1913 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-05-24
Sat 08:00 Chicago Midway (MDW) 11:20 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-02-14 through 2026-02-28
Mon-Fri 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-06 through 2026-01-14
Thu,Fri,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-01-11 through 2026-01-16
Tue-Fri,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-18 through 2026-01-23
Mon,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-01-19 through 2026-01-25
Mon-Fri 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-01-26 through 2026-02-04
Thu,Fri,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-02-01 through 2026-02-06
Tue,Wed,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-08 through 2026-02-11
Mon,Sun 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-02-17 through 2026-02-23
Tue,Wed 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-18 through 2026-03-04
Mon 13:35 Chicago Midway (MDW) 16:50 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-03-02
Mon,Thu,Fri 14:10 Chicago Midway (MDW) 17:25 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 14:10 Chicago Midway (MDW) 17:25 Jacksonville (JAX)
Southwest Airlines WN 2698 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-20 through 2026-03-01
Tue,Wed 18:20 Chicago Midway (MDW) 21:40 Jacksonville (JAX)
Southwest Airlines WN 2792 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 19:20 Chicago Midway (MDW) 22:35 Jacksonville (JAX)
Southwest Airlines WN 2792 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-04 through 2026-08-03
Sat 20:40 Chicago Midway (MDW) 23:55 Jacksonville (JAX)
Southwest Airlines WN 2846 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2026-01-03
Mon 11:05 Chicago Midway (MDW) 14:20 Jacksonville (JAX)
Southwest Airlines WN 3123 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-01-05
Thu 13:40 Chicago Midway (MDW) 16:55 Jacksonville (JAX)
Southwest Airlines WN 3123 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-01
Tue,Wed 17:55 Chicago Midway (MDW) 21:15 Jacksonville (JAX)
Southwest Airlines WN 3126 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-04 through 2026-09-30
Sun 18:50 Chicago Midway (MDW) 22:05 Jacksonville (JAX)
Southwest Airlines WN 3535 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Mon,Tue,Fri,Sun 10:45 Chicago Midway (MDW) 14:00 Jacksonville (JAX)
Southwest Airlines WN 3721 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-04
Sat 07:50 Chicago Midway (MDW) 11:15 Jacksonville (JAX)
Southwest Airlines WN 4499 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 08:40 Chicago Midway (MDW) 12:00 Jacksonville (JAX)
Southwest Airlines WN 4499 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-04 through 2026-08-03
Sun 11:35 Chicago Midway (MDW) 14:50 Jacksonville (JAX)
Southwest Airlines WN 4499 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-07 through 2026-08-02
Sat 12:45 Chicago Midway (MDW) 16:00 Jacksonville (JAX)
Southwest Airlines WN 4587 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-08 through 2026-09-26
Mon,Thu,Fri 18:45 Chicago Midway (MDW) 22:00 Jacksonville (JAX)
Southwest Airlines WN 4587 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-06 through 2026-09-28
Non-Direct Flights:
Tue,Wed 16:50 Chicago Midway (MDW) 21:30 Jacksonville (JAX)
Southwest Airlines WN 3235 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-04-07 through 2026-06-03


All airlines flying from Chicago Midway (MDW) to Jacksonville (JAX).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

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:

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:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

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:

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:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

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:

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:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

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:

Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

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:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Valid until 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Valid until 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

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:

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:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Chicago Midway airport (MDW) and arriving at Jacksonville airport (JAX).
  • The flight distance is 849 miles, or 1367 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 2:15 and 2:25.