Southwest Airlines flights from Chicago O'Hare (ORD) to Fort Myers (RSW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 11:55 Chicago O'Hare (ORD) 5 15:55 Fort Myers (RSW)
Southwest Airlines WN 3055 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-02-12 through 2026-02-16
Sat 11:55 Chicago O'Hare (ORD) 5 15:55 Fort Myers (RSW)
Southwest Airlines WN 3055 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-02-14 through 2026-02-28
Thu,Fri,Sun 11:55 Chicago O'Hare (ORD) 5 15:55 Fort Myers (RSW)
Southwest Airlines WN 3055 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-02-20 through 2026-03-01
Sat 09:55 Chicago O'Hare (ORD) 5 13:50 Fort Myers (RSW)
Southwest Airlines WN 3690 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri,Sun 10:30 Chicago O'Hare (ORD) 5 14:25 Fort Myers (RSW)
Southwest Airlines WN 3690 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-04-09 through 2026-05-22
Sun 10:30 Chicago O'Hare (ORD) 5 14:25 Fort Myers (RSW)
Southwest Airlines WN 3690 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-05-24
Mon,Thu,Fri,Sun 10:30 Chicago O'Hare (ORD) 5 14:25 Fort Myers (RSW)
Southwest Airlines WN 3690 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-05-25 through 2026-06-01
Mon,Tue,Fri,Sun 11:55 Chicago O'Hare (ORD) 5 15:50 Fort Myers (RSW)
Southwest Airlines WN 4053 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Valid until 2026-01-04
Sat 11:55 Chicago O'Hare (ORD) 5 15:50 Fort Myers (RSW)
Southwest Airlines WN 4053 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Operates only on 2026-01-03
Daily 10:30 Chicago O'Hare (ORD) 5 14:25 Fort Myers (RSW)
Southwest Airlines WN 4153 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-05 through 2026-04-06
Non-Direct Flights:
Sat 15:45 Chicago O'Hare (ORD) 5 21:15 Fort Myers (RSW)
Southwest Airlines WN 658 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-06-06 through 2026-08-01




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Southwest Airlines flights from Chicago O'Hare (ORD) to Fort Myers (RSW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN3055
11:55
Chicago O'Hare (ORD) 5

15:55
Fort Myers (RSW)
Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:00, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN3055
11:55
Chicago O'Hare (ORD) 5

15:55
Fort Myers (RSW)
Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:00, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3055
11:55
Chicago O'Hare (ORD) 5

15:55
Fort Myers (RSW)
Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:00, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN3690
09:55
Chicago O'Hare (ORD) 5

13:50
Fort Myers (RSW)
Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:55, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN3690
10:30
Chicago O'Hare (ORD) 5

14:25
Fort Myers (RSW)
Effective 2026-04-09 through 2026-05-22
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737-800 (73H)
Direct Flights:
Southwest Airlines WN3690
10:30
Chicago O'Hare (ORD) 5

14:25
Fort Myers (RSW)
Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN3690
10:30
Chicago O'Hare (ORD) 5

14:25
Fort Myers (RSW)
Effective 2026-05-25 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737-800 (73H)
Direct Flights:
Southwest Airlines WN4053
11:55
Chicago O'Hare (ORD) 5

15:50
Fort Myers (RSW)
Valid until 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN4053
11:55
Chicago O'Hare (ORD) 5

15:50
Fort Myers (RSW)
Operates only on 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:55, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN4153
10:30
Chicago O'Hare (ORD) 5

14:25
Fort Myers (RSW)
Effective 2026-03-05 through 2026-04-06
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Duration: 2:55, non-stop
Boeing 737-800 (73H)
Non-Direct Flights:
Southwest Airlines WN658
15:45
Chicago O'Hare (ORD) 5

21:15
Fort Myers (RSW)
Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Chicago O'Hare airport (ORD) and arriving at Fort Myers airport (RSW).
  • The flight distance is 1122 miles, or 1806 km.
  • The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-5 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
  • For direct flights, the flight time varies between 2:55 and 3:00.
All ORD-RSW flights
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