Airlines with flights from Jacksonville to Chicago
There are three airlines with scheduled flights between JAX and MDW. Southwest is the only airline with non-stop flights from Jacksonville International to Midway International Airport and the flight time is 2 hours and 30 minutes.
There are three airlines with scheduled flights between JAX and MDW. Southwest is the only airline with non-stop flights from Jacksonville International to Midway International Airport and the flight time is 2 hours and 30 minutes. Choose airline
Direct
Non-stop
2h 30min
Via Nashville
3h 50min
Via Saint Louis
3h 50min
Via Atlanta
3h 54min
Via Atlanta
4h 29min
Via Baltimore
4h 35min
NEW
Starts 03/10
Via Washington
6h 45min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 30 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
15 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
JAX
Direct
MDW
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
WN1384
07:45
07:25
07:25
07:45
07:45
10:55
07:45
WN2164
19:15
18:45
18:45
19:15
19:15
----
17:50
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 3h 50m - 7h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
63 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
JAX
Via BNA
MDW
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
WN2155
WN1473
WN1473
----
06:45
06:45
----
----
----
----
WN2156
WN1430
WN1430
----
----
----
----
----
11:55
----
WN2156
WN2241
WN2241
----
13:55
13:55
----
----
----
----
WN2157
WN578
WN578
20:55
20:15
20:15
20:55
20:55
20:10
21:10
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 3h 50m - 8h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
13 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
JAX
Via STL
MDW
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
WN2547
WN2570
WN2570
----
----
----
----
----
----
06:05
WN2087
WN1373
WN1373
----
08:25
08:25
----
----
----
----
WN449
WN3957
WN3957
----
----
----
----
----
18:20
19:55
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 3h 54m - 6h 09m.
-
Sky Team Alliance
-
157 flights per week
JAX
Via ATL
MDW
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
DL2722
DL1063
DL1063
05:30
05:30
05:30
05:30
05:30
05:30
05:30
DL2450
DL1063
DL1063
07:00
07:00
07:00
07:00
07:00
07:00
07:00
DL2569
DL2417
DL2417
08:10
08:10
08:10
08:10
08:10
----
08:10
DL2326
DL2417
DL2417
----
----
----
----
----
10:44
----
DL2356
DL1728
DL1728
11:50
11:50
11:50
11:50
11:50
----
11:50
DL2356
DL2417
DL2417
----
----
----
----
----
11:50
----
DL2923
DL1728
DL1728
13:05
13:05
13:05
13:05
13:05
----
13:05
DL2720
DL1076
DL1076
17:33
17:33
17:33
17:33
17:33
17:44
17:33
DL2627
DL1076
DL1076
18:58
18:58
18:58
18:58
18:58
18:58
18:58
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Frontier Airlines
-
Total flight time: 4h 29m - 4h 54m.
-
Low-cost airline
-
Chicago is a Frontier Airlines focus city (Operating base).
-
6 flights per week
JAX
Via ATL
MDW
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
F93083
F92291
F92291
18:28
18:28
18:28
18:28
18:28
18:28
18:28
The timetable & schedule information was updated at 2026-04-21
