Airlines with flights from Chicago to Jacksonville
There are three airlines with scheduled flights between MDW and JAX. Southwest is the only airline with non-stop flights from Midway International Airport to Jacksonville International and the flight time is 2 hours and 15 minutes.
There are three airlines with scheduled flights between MDW and JAX. Southwest is the only airline with non-stop flights from Midway International Airport to Jacksonville International and the flight time is 2 hours and 15 minutes. Choose airline
Direct
Non-stop
2h 15min
Via Nashville
3h 35min
Via Saint Louis
3h 55min
Via Atlanta
3h 57min
Via Atlanta
4h 16min
Via Baltimore
4h 30min
Starts 07/06
Via Indianapolis
7h 50min
NEW
Starts 06/09
Via Kansas City
6h 40min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 15 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
16 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
JAX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4499
08:40
----
----
08:40
08:40
07:50
11:35
WN1780
----
12:50
12:50
----
----
----
----
WN2792
19:20
18:20
18:20
19:20
19:20
----
----
WN3535
----
----
----
----
----
----
18:50
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 3h 35m - 7h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
92 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via BNA
JAX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2959
WN541
WN541
07:15
----
----
07:15
07:15
----
----
WN1775
WN542
WN542
07:55
----
----
07:55
07:55
----
----
WN1775
WN541
WN541
----
----
----
----
----
----
08:30
WN2733
WN542
WN542
11:20
----
----
11:20
11:20
----
----
WN533
WN542
WN542
----
----
----
----
----
----
11:50
WN3869
WN4624
WN4624
----
15:10
15:10
----
----
----
----
WN3614
WN4624
WN4624
----
----
----
----
----
----
16:40
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 3h 55m - 8h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
25 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via STL
JAX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2900
WN4081
WN4081
----
----
----
----
----
06:30
----
WN2900
WN270
WN270
----
----
----
----
----
----
08:05
WN2900
WN3771
WN3771
----
08:20
08:20
----
----
----
----
WN2902
WN3933
WN3933
13:00
----
----
13:00
13:00
----
----
WN103
WN3933
WN3933
----
----
----
----
----
14:35
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 3h 57m - 6h 15m.
-
Sky Team Alliance
-
132 flights per week
MDW
Via ATL
JAX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL1285
DL2923
DL2923
06:05
06:05
06:05
06:05
06:05
06:05
06:05
DL1063
DL2720
DL2720
11:05
11:05
11:05
11:05
11:05
10:55
11:05
DL2417
DL2627
DL2627
12:45
12:45
12:45
12:45
12:45
----
12:45
DL1728
DL1001
DL1001
17:11
----
----
17:11
17:11
----
17:11
DL1728
DL2276
DL2276
17:11
17:11
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Frontier Airlines
-
Total flight time: 4h 16m - 5h 37m.
-
Low-cost airline
-
Chicago is a Frontier Airlines focus city (Operating base).
-
3 flights per week
MDW
Via ATL
JAX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
F92144
F91550
F91550
12:04
----
12:04
----
12:04
11:59
----
The timetable & schedule information was updated at 2026-04-21
