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Direct flights from Jacksonville to Chicago

Airlines Schedules

JAX - MDW route map All flights from JAX to MDW non-stop. There are direct flights from Jacksonville International (JAX), Florida, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 13 weekly departures are currently scheduled on this route. Departure times range from 07:00 to 19:55 depending on the schedule period. The flight distance is 854 miles (1374 km). Flight time ranges from 2 hours and 20 minutes to 2 hours and 30 minutes.

JAX
Jacksonville
USAJacksonville , USA
MDW
Chicago Midway
USAChicago , USA
JAX
Jacksonville
USAJacksonville , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 2h 20min to 2h 30min
Updated Jun 15, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 07:00 and 19:55
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
13 flights/week
13 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Jacksonville to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Jul 13
Tue
Jul 14
Wed
Jul 15
Thu
Jul 16
Fri
Jul 17
Sat
Jul 18
Sun
Jul 19
WN1384
07:45
07:25
07:25
07:45
07:45
10:55
07:45
WN2164
19:15
18:50
18:50
19:15
19:15
----
17:50

The timetable & schedule information was updated at 2026-06-15

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Jacksonville to Chicago scheduled departures

Select a date to see every published non-stop departure between JAX and MDW.

Monday
Mon
Jul 13
2 flights(2)
Tuesday
Tue
Jul 14
2 flights(2)
Wednesday
Wed
Jul 15
2 flights(2)
Thursday
Thu
Jul 16
2 flights(2)
Friday
Fri
Jul 17
2 flights(2)
Saturday
Sat
Jul 18
1 flights(1)
Sunday
Sun
Jul 19
2 flights(2)
Time
Airline
Flight
07:45
Southwest Airlines Southwest Airlines
WN1384
19:15
Southwest Airlines Southwest Airlines
WN2164
07:25
Southwest Airlines Southwest Airlines
WN1384
18:50
Southwest Airlines Southwest Airlines
WN2164
07:25
Southwest Airlines Southwest Airlines
WN1384
18:50
Southwest Airlines Southwest Airlines
WN2164
07:45
Southwest Airlines Southwest Airlines
WN1384
19:15
Southwest Airlines Southwest Airlines
WN2164
07:45
Southwest Airlines Southwest Airlines
WN1384
19:15
Southwest Airlines Southwest Airlines
WN2164
10:55
Southwest Airlines Southwest Airlines
WN1384
07:45
Southwest Airlines Southwest Airlines
WN1384
17:50
Southwest Airlines Southwest Airlines
WN2164
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JAX-MDW flight route
Route map from Jacksonville, JAX to Chicago, MDW. The distance is 854 miles or 1374 km.
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Jacksonville - Chicago direct flight map
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JAX - MDW route facts

  • Distance
    854 miles (1374 km)
  • Flight time
    2 hours and 20 minutes to 2 hours and 30 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737-800 (winglets) Passenger/BBJ2

Route FAQ

Southwest Airlines operates non-stop flights from JAX to MDW with 13 weekly departures.

Scheduled flight time from JAX to MDW ranges from 2 hours and 20 minutes to 2 hours and 30 minutes. The route covers 854 miles (1374 km).

13 weekly departures are currently scheduled on this route, with published departure times ranging from 07:00 to 19:55 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
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