Airlines with flights from Chicago to Orlando

There are three airlines with scheduled flights between MDW and MCO. Both Southwest and Frontier operates non-stop flights from Midway International Airport to Orlando International and the flight time is 2 hours and 35 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 35 minutes
  • Low-cost airline
  • Chicago and Orlando are both Southwest Airlines focus cities.
  • 54 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
Direct
MCO
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2758
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06:15
06:15
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05:00
05:10
WN801
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05:00
05:00
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WN2815
05:10
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WN2816
06:30
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WN118
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07:25
07:25
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WN636
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08:30
08:30
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07:45
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WN2817
08:00
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WN3060
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08:05
WN3245
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09:10
09:10
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WN2764
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09:40
09:40
14:55
14:55
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09:40
WN2818
11:00
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WN1854
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11:15
11:15
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WN376
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12:20
12:20
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WN2819
13:40
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WN4933
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15:40
15:40
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15:40
14:15
WN164
17:10
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WN260
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18:00
WN491
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18:20
18:20
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WN2820
18:35
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WN2763
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19:50
19:50
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WN1417
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20:05
WN2821
20:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

Frontier Airlines

Non-stop with Frontier Airlines

  • Total flight time: 2 hours and 50 minutes
  • Low-cost airline
  • Chicago and Orlando are both Frontier Airlines focus cities.
  • 2 flights per week
MDW
Direct
MCO
 
Flight
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 3h 55m - 8h 05m.
  • Low-cost airline
  • Chicago and Orlando are both Southwest Airlines focus cities.
  • 157 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via BNA
 
MCO
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN508
WN578
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05:55
05:55
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WN2959
WN4206
07:15
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WN2675
WN1753
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07:30
WN1409
WN693
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07:40
07:40
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WN1799
WN447
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07:55
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WN1775
WN4714
07:55
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WN120
WN603
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08:00
08:00
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WN2676
WN564
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08:05
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WN485
WN564
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08:50
08:50
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WN442
WN1358
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08:50
WN1257
WN4714
09:00
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WN2676
WN1291
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09:05
09:05
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WN2675
WN2966
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11:00
11:00
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WN2733
WN569
11:20
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WN1585
WN564
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11:40
WN240
WN494
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12:35
12:35
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WN512
WN494
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13:15
WN1035
WN365
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13:55
WN2677
WN4483
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14:25
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WN3869
WN572
17:05
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WN4859
WN569
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17:20
17:20
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WN2677
WN1358
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17:30
17:30
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WN1794
WN4995
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18:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

Southwest Airlines

Via Atlanta with Southwest Airlines

  • Total flight time: 3h 55m - 6h 15m.
  • Low-cost airline
  • Chicago and Orlando are both Southwest Airlines focus cities.
  • 60 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via ATL
 
MCO
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4796
WN2177
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07:40
06:05
WN3054
WN215
07:15
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WN2522
WN2724
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08:10
08:10
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WN2828
WN363
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08:40
08:40
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WN3442
WN463
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09:55
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WN487
WN463
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12:50
12:50
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WN1934
WN463
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13:10
WN3459
WN1740
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13:20
13:20
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WN4592
WN4558
14:40
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WN2414
WN1740
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15:10
15:10
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

Southwest Airlines

Via Indianapolis with Southwest Airlines

  • Total flight time: 4h 00m - 7h 45m.
  • Low-cost airline
  • Chicago and Orlando are both Southwest Airlines focus cities.
  • 23 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via IND
 
MCO
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4768
WN2274
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10:10
10:10
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WN4768
WN2069
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10:20
10:20
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

Southwest Airlines

Via Louisville with Southwest Airlines

  • Total flight time: 4h 00m - 6h 15m.
  • Low-cost airline
  • Chicago and Orlando are both Southwest Airlines focus cities.
  • 18 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via SDF
 
MCO
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4473
WN910
12:45
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WN512
WN1492
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13:15
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - MCO

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

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Flight data on this page was last updated on 2026-07-13
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