Airlines with flights from Chicago to Fort Myers

There are two airlines with scheduled flights between MDW and RSW. Southwest is the only airline with non-stop flights from Midway International Airport to Southwest Florida International Airport and the flight time is 2 hours and 45 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 45 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 27 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
RSW
 
Flight
Mon
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
WN4151
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05:05
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WN3481
09:00
07:40
07:40
09:00
09:00
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WN3016
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08:40
WN3224
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13:15
13:15
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WN4764
14:50
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14:50
14:50
13:30
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WN2881
18:55
18:55
18:55
18:55
18:55
17:55
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WN997
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19:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - RSW

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 10m - 8h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 90 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via BNA
 
RSW
 
Flight
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Jun 15
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Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN1708
WN657
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07:45
07:45
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WN1775
WN657
07:55
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07:55
07:55
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08:30
WN1257
WN657
09:00
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09:00
09:00
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WN2733
WN657
11:20
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11:20
11:20
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WN3869
WN658
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15:10
15:10
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WN1257
WN658
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15:30
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WN3614
WN658
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16:40
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - RSW

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

Southwest Airlines

Via Orlando with Southwest Airlines

  • Total flight time: 4h 10m - 9h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 88 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via MCO
 
RSW
 
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
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Jun 21
WN435
WN4709
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12:00
WN2877
WN4709
13:20
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----
13:20
13:20
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12:00
WN3579
WN4709
12:40
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12:40
12:40
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WN692
WN1353
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12:50
12:50
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WN114
WN4709
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12:50
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WN692
WN4709
13:30
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----
13:30
13:30
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WN160
WN4709
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13:35
WN2819
WN1353
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14:50
14:50
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WN1779
WN4709
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14:50
WN496
WN1353
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15:00
15:00
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WN2820
WN4709
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15:50
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WN2817
WN1353
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16:35
16:35
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - RSW

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

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 15m - 9h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 62 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via STL
 
RSW
 
Flight
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Jun 15
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Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2900
WN234
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06:30
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WN2900
WN4940
07:50
08:20
08:20
07:50
07:50
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08:05
WN2902
WN2653
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----
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13:10
WN2904
WN4831
18:00
17:10
17:10
18:00
18:00
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WN1646
WN4831
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----
----
----
----
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18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - RSW

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

Southwest Airlines

Via Indianapolis with Southwest Airlines

  • Total flight time: 4h 20m - 6h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 15 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via IND
 
RSW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN3877
WN2137
10:00
10:10
10:10
10:00
10:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - RSW

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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