Airlines with flights from Orlando to Chicago

There are three airlines with scheduled flights between MCO and MDW. Southwest is the only airline with non-stop flights from Orlando International to Midway International Airport and the flight time is 2 hours and 55 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 55 minutes
  • Low-cost airline
  • Orlando and Chicago are both Southwest Airlines focus cities.
  • 70 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MCO
Direct
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 21
WN2654
07:25
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07:25
07:25
07:00
06:45
WN2560
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07:10
07:10
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WN2835
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08:00
08:00
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08:00
07:45
WN1340
08:15
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08:15
08:15
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WN4037
09:10
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09:10
09:10
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WN2653
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11:00
11:00
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WN2657
13:00
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13:00
13:00
13:25
17:30
WN3874
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13:30
13:30
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WN5067
14:30
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14:30
14:30
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WN2658
16:05
14:30
14:30
16:05
16:05
15:25
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WN2617
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15:20
WN2659
18:10
16:20
16:20
18:10
18:10
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WN1255
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16:30
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WN2660
19:35
18:15
18:15
19:35
19:35
18:25
18:50
WN4762
22:55
20:10
20:10
22:55
22:55
21:55
22:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR MCO - MDW

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

Southwest Airlines

Via Columbus with Southwest Airlines

  • Total flight time: 4h 00m - 6h 30m.
  • Low-cost airline
  • Orlando and Chicago are both Southwest Airlines focus cities.
  • 50 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MCO
 
Via CMH
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 20
Sun
Jun 21
WN2616
WN1197
06:10
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06:10
06:10
06:10
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WN2616
WN1198
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07:05
07:05
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WN3402
WN66
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14:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MCO - MDW

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

Southwest Airlines

Via Atlanta with Southwest Airlines

  • Total flight time: 4h 05m - 7h 20m.
  • Low-cost airline
  • Orlando and Chicago are both Southwest Airlines focus cities.
  • 67 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MCO
 
Via ATL
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2591
WN225
08:00
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08:00
08:00
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WN2591
WN2048
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08:00
WN2466
WN3903
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08:00
08:00
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WN4922
WN233
15:10
15:10
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WN4922
WN232
15:30
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15:30
15:30
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15:15
WN3671
WN335
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16:10
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MCO - MDW

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 10m - 8h 45m.
  • Low-cost airline
  • Orlando and Chicago are both Southwest Airlines focus cities.
  • 218 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MCO
 
Via BNA
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 20
Sun
Jun 21
WN2510
WN1473
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06:20
06:20
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WN2603
WN2741
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06:40
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WN550
WN507
07:35
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07:35
07:35
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WN684
WN1430
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08:00
08:00
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WN2764
WN507
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08:00
08:00
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WN2604
WN1430
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09:35
09:35
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WN550
WN1009
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09:35
WN4713
WN1430
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10:55
10:55
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WN2605
WN2241
12:15
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12:15
12:15
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WN2604
WN478
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12:35
WN2605
WN1430
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13:05
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WN2605
WN478
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13:45
WN2566
WN478
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14:40
WN1220
WN4277
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16:30
WN2606
WN4286
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16:40
16:40
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WN2839
WN578
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17:10
17:10
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WN4711
WN4286
17:20
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17:20
17:20
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WN2607
WN4277
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18:10
WN2607
WN578
19:40
18:15
18:15
19:40
19:40
19:00
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WN2071
WN578
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18:50
WN4711
WN578
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20:00
19:00
WN2608
WN578
20:45
19:45
19:45
20:45
20:45
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20:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR MCO - MDW

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

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 15m - 9h 45m.
  • Low-cost airline
  • Orlando and Chicago are both Southwest Airlines focus cities.
  • 132 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MCO
 
Via STL
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 19
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Jun 20
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Jun 21
WN2615
WN2665
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06:10
06:10
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WN2828
WN2570
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06:55
WN4501
WN3344
08:50
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08:50
08:50
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WN4501
WN1373
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08:50
08:50
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WN4501
WN2832
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08:55
WN3316
WN556
11:10
13:45
13:45
11:10
11:10
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WN3316
WN2468
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12:00
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WN1574
WN556
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13:55
WN5048
WN2289
14:05
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14:05
14:05
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WN2679
WN3957
14:40
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14:40
14:40
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WN3236
WN3957
19:00
18:40
18:40
19:00
19:00
18:15
18:10
SHOW RETURN SCHEDULE
CHECK PRICES FOR MCO - MDW

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

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Flight data on this page was last updated on 2026-06-02
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