Airlines with flights from Fort Myers to Chicago
There are two airlines with scheduled flights between RSW and MDW. Southwest is the only airline with non-stop flights from Southwest Florida International Airport to Midway International Airport and the flight time is 2 hours and 55 minutes.
There are two airlines with scheduled flights between RSW and MDW. Southwest is the only airline with non-stop flights from Southwest Florida International Airport to Midway International Airport and the flight time is 2 hours and 55 minutes. Choose airline
Direct
Non-stop
2h 55min
Via Saint Louis
4h 15min
Via Orlando
4h 15min
Via Columbus
4h 15min
Via Indianapolis
4h 15min
Via Atlanta
4h 25min
Via Nashville
4h 25min
Via Milwaukee
4h 25min
Via Pittsburgh
4h 30min
Via Detroit
5h 2min
Via Baltimore
5h 5min
Via Kansas City
5h 15min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 55 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
26 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
RSW
Direct
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1243
05:10
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----
05:10
05:10
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----
WN1439
----
07:10
07:10
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----
----
----
WN3665
----
----
----
----
----
----
07:20
WN4120
17:10
18:25
18:25
17:10
17:10
07:40
----
WN3469
11:40
12:10
12:10
11:40
11:40
11:40
----
WN3398
----
----
----
----
----
----
17:10
WN4085
----
----
----
----
----
18:00
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The timetable & schedule information was updated at 2026-04-22
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 15m - 9h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
76 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
RSW
Via STL
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3471
WN2570
WN2570
05:55
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----
05:55
05:55
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06:00
WN3471
WN2665
WN2665
----
06:00
06:00
----
----
----
----
WN3472
WN3957
WN3957
19:20
18:55
18:55
19:20
19:20
----
19:30
The timetable & schedule information was updated at 2026-04-22
Via Orlando with Southwest Airlines
-
Total flight time: 4h 15m - 8h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
71 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
RSW
Via MCO
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4872
WN2835
WN2835
06:15
06:10
06:10
06:15
06:15
06:20
06:10
The timetable & schedule information was updated at 2026-04-22
Via Columbus with Southwest Airlines
-
Total flight time: 4h 15m - 6h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
37 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
RSW
Via CMH
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3790
WN1197
WN1197
----
----
----
----
----
05:35
----
WN3466
WN1200
WN1200
----
14:30
14:30
----
----
----
----
The timetable & schedule information was updated at 2026-04-22
Via Indianapolis with Southwest Airlines
-
Total flight time: 4h 15m - 6h 25m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
16 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
RSW
Via IND
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3467
WN2290
WN2290
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----
----
----
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13:00
The timetable & schedule information was updated at 2026-04-22
Via Atlanta with Delta