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.

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Schedules

Southwest Airlines

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).
  • 13 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
JAX
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
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Aug 5
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Aug 6
Fri
Aug 7
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Aug 8
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Aug 9
WN1768
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07:00
07:00
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WN2099
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07:30
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WN1384
07:45
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WN981
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17:25
17:25
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WN673
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17:35
WN2164
19:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
JAX
 
Via BNA
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4231
WN4895
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06:45
06:45
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WN2467
WN573
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07:25
07:25
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WN2092
WN573
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11:20
WN2315
WN575
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13:00
13:00
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WN2092
WN575
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14:05
14:05
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WN2117
WN576
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15:55
WN2093
WN4549
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16:10
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WN2093
WN577
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18:50
18:50
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WN2117
WN4549
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19:15
19:15
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WN2157
WN578
20:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
JAX
 
Via STL
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1686
WN2814
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06:25
WN4975
WN3862
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06:40
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WN1097
WN3862
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07:50
07:50
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WN2792
WN2052
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12:25
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SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Atlanta with Delta Air Lines

  • Total flight time: 3h 54m - 6h 09m.
  • Sky Team Alliance
  • 157 flights per week
JAX
 
Via ATL
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
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Aug 9
DL2722
DL1063
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL2450
DL1063
07:00
07:00
07:00
07:00
07:00
07:00
07:00
DL2569
DL2417
08:10
08:10
08:10
08:10
08:10
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08:10
DL2326
DL2417
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10:44
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DL2356
DL1728
11:48
11:48
11:48
11:48
11:48
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11:48
DL2356
DL2417
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11:48
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DL2923
DL1728
12:50
12:50
12:50
12:50
12:50
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12:50
DL2720
DL1076
17:32
17:34
17:34
17:32
17:32
17:34
17:32
DL2627
DL1076
18:58
18:58
18:58
18:58
18:58
18:58
18:58
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2026-04-21

Frontier Airlines

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
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
F93083
F92291
18:28
18:28
18:28
18:28
18:28
18:28
18:28
SHOW RETURN SCHEDULE
CHECK PRICES FOR JAX - MDW

The timetable & schedule information was updated at 2026-04-21

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Flight data on this page was last updated on 2026-07-21
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