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.
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. Choose airline
Direct
Non-stop
2h 45min
Via Nashville
4h 10min
Via Orlando
4h 10min
Via Saint Louis
4h 15min
Via Indianapolis
4h 20min
Via Pittsburgh
4h 25min
Via Atlanta
4h 34min
Via Columbus
4h 50min
Via Kansas City
4h 50min
Via Baltimore
5h 15min
Via Detroit
6h 11min
Via Buffalo
6h 25min
Via Cleveland
7h 35min
Schedules
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).
-
20 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Direct
RSW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4034
----
08:50
08:50
----
----
11:00
----
WN1575
----
----
----
09:00
09:00
----
09:00
WN3481
09:00
----
----
----
----
----
----
WN1155
----
----
----
13:00
13:00
----
----
WN4764
14:50
----
----
----
----
----
----
WN4479
----
----
----
----
----
15:05
----
WN2813
----
18:00
18:00
----
----
----
18:55
WN356
----
----
----
18:15
18:15
----
----
WN2881
18:55
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via BNA
RSW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1775
WN657
WN657
07:55
----
----
----
----
----
----
WN120
WN2253
WN2253
----
----
----
08:00
08:00
----
----
WN442
WN1479
WN1479
----
----
----
----
----
----
08:50
WN1257
WN657
WN657
09:00
----
----
----
----
----
----
WN2676
WN1479
WN1479
----
09:05
09:05
----
----
----
----
WN2733
WN657
WN657
11:20
----
----
----
----
----
----
WN240
WN1017
WN1017
----
12:35
12:35
----
----
----
----
WN1704
WN1017
WN1017
----
13:00
13:00
----
----
----
----
WN2677
WN1017
WN1017
----
14:40
14:40
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via MCO
RSW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN801
WN1405
WN1405
----
----
----
05:00
05:00
----
----
WN2758
WN2640
WN2640
----
06:15
06:15
----
----
05:00
05:10
WN397
WN2641
WN2641
----
----
----
----
----
09:20
----
WN376
WN1268
WN1268
----
12:20
12:20
----
----
----
----
WN3579
WN4709
WN4709
12:40
----
----
----
----
----
----
WN1377
WN2641
WN2641
----
----
----
13:00
13:00
----
----
WN2877
WN4709
WN4709
13:20
----
----
----
----
----
----
WN692
WN4709
WN4709
13:30
----
----
----
----
----
----
WN4933
WN2354
WN2354
----
----
----
----
----
----
14:15
WN1961
WN2354
WN2354
----
----
----
----
----
----
14:45
WN2764
WN2641
WN2641
----
----
----
14:55
14:55
----
----
WN856
WN2354
WN2354
----
----
----
----
----
----
15:00
WN2839
WN2641
WN2641
----
----
----
15:10
15:10
----
----
The timetable & schedule information was updated at 2026-04-21
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via STL
RSW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2837
WN4210
WN4210
----
----
----
----
----
06:35
----
WN2900
WN4940
WN4940
07:50
----
----
----
----
----
----
WN2837
WN1282
WN1282
----
----
----
----
----
----
07:55
WN2837
WN3884
WN3884
----
08:15
08:15
----
----
----
----
WN2839
WN22
WN22
----
----
----
----
----
----
13:30
WN2839
WN4074
WN4074
----
----
----
15:10
15:10
----
----
WN126
WN4074
WN4074
----
16:40
16:40
----
----
----
----
WN2904
WN4831
WN4831
18:00
----
----
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via IND
RSW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3877
WN2137
WN2137
10:00
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----
----
----
----
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WN4768
WN4067
WN4067
----
----
----
10:10
10:10
----
----
WN3330
WN3262
WN3262
----
----
----
----
----
----
10:15
WN4768
WN3262
WN3262
----
10:20
10:20
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta