Airlines with flights from Jacksonville to Chicago

There are two 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.

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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).
  • 9 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
JAX
Direct
MDW
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN4816
17:20
16:20
16:35
16:20
17:20
07:00
17:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2025-01-15

Via Atlanta with Delta Air Lines

  • Total flight time: 3h 48m - 6h 12m.
  • Sky Team Alliance
  • 39 flights per week
JAX
 
Via ATL
 
MDW
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL2722
DL1063
05:35
05:35
05:35
05:35
05:35
----
05:35
DL2440
DL1063
06:39
06:39
06:39
06:39
06:39
06:00
06:39
DL2446
DL2417
08:00
08:00
08:00
08:00
08:00
----
08:00
DL2326
DL1739
11:27
11:27
11:27
11:27
11:27
11:27
11:27
DL2333
DL3869
----
----
----
----
----
11:50
----
DL2720
DL1076
17:48
17:48
17:48
17:48
17:48
17:48
17:48
DL2627
DL1076
18:59
18:59
18:59
18:59
18:59
----
18:59
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2025-01-15

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 40m - 9h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 13 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
JAX
 
Via BWI
 
MDW
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN441
WN1580
----
----
----
----
----
06:00
----
WN441
WN1048
06:10
----
07:10
----
06:10
----
06:10
WN441
WN1797
----
06:20
----
06:20
----
----
----
WN699
WN4877
06:50
----
----
----
06:50
----
06:50
WN699
WN553
06:50
----
----
----
06:50
----
06:50
WN968
WN1601
----
----
----
----
----
07:25
----
WN968
WN5265
----
----
07:55
----
----
----
----
WN591
WN849
10:50
----
----
----
10:50
----
10:50
WN683
WN519
----
----
11:45
----
----
----
----
WN2151
WN2906
----
11:50
----
11:50
----
----
----
WN1475
WN2756
----
----
----
----
----
11:55
----
WN1953
WN2221
----
12:30
----
12:30
----
----
----
WN2882
WN4710
15:50
----
----
----
15:50
----
15:50
WN3375
WN491
----
----
----
----
----
17:00
----
WN714
WN4710
----
18:05
----
18:05
----
----
----
WN2151
WN2455
18:55
----
----
----
18:55
----
18:55
WN3037
WN2965
----
----
19:10
----
----
----
----
WN3965
WN4703
----
19:15
----
19:15
----
----
----
WN3037
WN1647
21:05
19:55
----
19:55
21:05
----
21:05
WN3170
WN4877
----
----
----
----
----
20:00
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2025-01-15

Via Atlanta with Southwest Airlines

  • Total flight time: 3h 55m - 6h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 8 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
JAX
 
Via ATL
 
MDW
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN441
WN1580
----
----
----
----
----
06:00
----
WN441
WN1048
06:10
----
07:10
----
06:10
----
06:10
WN441
WN1797
----
06:20
----
06:20
----
----
----
WN699
WN4877
06:50
----
----
----
06:50
----
06:50
WN699
WN553
06:50
----
----
----
06:50
----
06:50
WN968
WN1601
----
----
----
----
----
07:25
----
WN968
WN5265
----
----
07:55
----
----
----
----
WN591
WN849
10:50
----
----
----
10:50
----
10:50
WN683
WN519
----
----
11:45
----
----
----
----
WN2151
WN2906
----
11:50
----
11:50
----
----
----
WN1475
WN2756
----
----
----
----
----
11:55
----
WN1953
WN2221
----
12:30
----
12:30
----
----
----
WN2882
WN4710
15:50
----
----
----
15:50
----
15:50
WN3375
WN491
----
----
----
----
----
17:00
----
WN714
WN4710
----
18:05
----
18:05
----
----
----
WN2151
WN2455
18:55
----
----
----
18:55
----
18:55
WN3037
WN2965
----
----
19:10
----
----
----
----
WN3965
WN4703
----
19:15
----
19:15
----
----
----
WN3037
WN1647
21:05
19:55
----
19:55
21:05
----
21:05
WN3170
WN4877
----
----
----
----
----
20:00
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2025-01-15

Via Nashville with Southwest Airlines

  • Total flight time: 3h 50m - 7h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 8 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
JAX
 
Via BNA
 
MDW
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN441
WN1580
----
----
----
----
----
06:00
----
WN441
WN1048
06:10
----
07:10
----
06:10
----
06:10
WN441
WN1797
----
06:20
----
06:20
----
----
----
WN699
WN4877
06:50
----
----
----
06:50
----
06:50
WN699
WN553
06:50
----
----
----
06:50
----
06:50
WN968
WN1601
----
----
----
----
----
07:25
----
WN968
WN5265
----
----
07:55
----
----
----
----
WN591
WN849
10:50
----
----
----
10:50
----
10:50
WN683
WN519
----
----
11:45
----
----
----
----
WN2151
WN2906
----
11:50
----
11:50
----
----
----
WN1475
WN2756
----
----
----
----
----
11:55
----
WN1953
WN2221
----
12:30
----
12:30
----
----
----
WN2882
WN4710
15:50
----
----
----
15:50
----
15:50
WN3375
WN491
----
----
----
----
----
17:00
----
WN714
WN4710
----
18:05
----
18:05
----
----
----
WN2151
WN2455
18:55
----
----
----
18:55
----
18:55
WN3037
WN2965
----
----
19:10
----
----
----
----
WN3965
WN4703
----
19:15
----
19:15
----
----
----
WN3037
WN1647
21:05
19:55
----
19:55
21:05
----
21:05
WN3170
WN4877
----
----
----
----
----
20:00
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2025-01-15

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