All airlines flying from Charleston (CHS) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Thu,Fri,Sun 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-01-11 through 2026-01-16
Mon,Sun 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-01 through 2026-02-06
Mon,Sun 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-17 through 2026-02-23
Mon 08:15 Charleston (CHS) 09:30 Chicago Midway (MDW) Southwest Airlines WN 403 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-03-02
Sat 08:00 Charleston (CHS) 09:15 Chicago Midway (MDW) Southwest Airlines WN 947 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-11 through 2026-05-30
Sun 18:00 Charleston (CHS) 19:20 Chicago Midway (MDW) Southwest Airlines WN 947 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2026-05-24
Sun 18:55 Charleston (CHS) 20:15 Chicago Midway (MDW) Southwest Airlines WN 947 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-12 through 2026-05-17
Sun 18:55 Charleston (CHS) 20:15 Chicago Midway (MDW) Southwest Airlines WN 947 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-31
Sat 06:00 Charleston (CHS) 07:15 Chicago Midway (MDW) Southwest Airlines WN 1078 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 19:30 Charleston (CHS) 20:45 Chicago Midway (MDW) Southwest Airlines WN 1078 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 19:30 Charleston (CHS) 20:45 Chicago Midway (MDW) Southwest Airlines WN 1078 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-02-20 through 2026-03-01
Tue,Wed 07:35 Charleston (CHS) 08:45 Chicago Midway (MDW) Southwest Airlines WN 1131 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-04 through 2026-09-30
Sat 07:35 Charleston (CHS) 08:45 Chicago Midway (MDW) Southwest Airlines WN 1131 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-08 through 2026-09-26
Sun 08:15 Charleston (CHS) 09:20 Chicago Midway (MDW) Southwest Airlines WN 1131 Non-stop Boeing 737-700 (Scimitar Winglets) 2:05 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 07:10 Charleston (CHS) 08:15 Chicago Midway (MDW) Southwest Airlines WN 1225 Non-stop Boeing 737 MAX 8 (7M8) 2:05 Effective 2026-08-06 through 2026-09-28
Tue,Wed 16:35 Charleston (CHS) 17:55 Chicago Midway (MDW) Southwest Airlines WN 1291 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-10 through 2026-04-01
Sun 18:30 Charleston (CHS) 19:40 Chicago Midway (MDW) Southwest Airlines WN 1516 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 18:35 Charleston (CHS) 19:45 Chicago Midway (MDW) Southwest Airlines WN 1516 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-06 through 2026-09-28
Mon 19:15 Charleston (CHS) 20:30 Chicago Midway (MDW) Southwest Airlines WN 1959 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-01-05
Sat 19:20 Charleston (CHS) 20:35 Chicago Midway (MDW) Southwest Airlines WN 1959 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-01-03
Mon,Tue,Fri,Sun 20:00 Charleston (CHS) 21:15 Chicago Midway (MDW) Southwest Airlines WN 1959 Non-stop Boeing 737-800 (73H) 2:15 Valid until 2026-01-04
Sat 18:15 Charleston (CHS) 19:30 Chicago Midway (MDW) Southwest Airlines WN 1962 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-06 through 2026-08-01
Sun 17:15 Charleston (CHS) 18:40 Chicago Midway (MDW) Southwest Airlines WN 2430 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-03-08 through 2026-04-05
Sat 18:55 Charleston (CHS) 20:20 Chicago Midway (MDW) Southwest Airlines WN 2430 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-03-07 through 2026-04-04
Sun 19:30 Charleston (CHS) 20:45 Chicago Midway (MDW) Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Tue,Wed 07:15 Charleston (CHS) 08:30 Chicago Midway (MDW) Southwest Airlines WN 3165 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 07:40 Charleston (CHS) 08:55 Chicago Midway (MDW) Southwest Airlines WN 3165 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-09 through 2026-06-01
Sun 07:40 Charleston (CHS) 08:55 Chicago Midway (MDW) Southwest Airlines WN 3165 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 07:40 Charleston (CHS) 08:55 Chicago Midway (MDW) Southwest Airlines WN 3165 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-05-31
Sun 08:50 Charleston (CHS) 10:05 Chicago Midway (MDW) Southwest Airlines WN 3165 Non-stop Boeing 737-800 (73H) 2:15 Operates only on 2026-05-24
Mon,Thu,Fri 17:45 Charleston (CHS) 19:05 Chicago Midway (MDW) Southwest Airlines WN 3304 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-03-05 through 2026-04-06
Sat 05:30 Charleston (CHS) 06:40 Chicago Midway (MDW) Southwest Airlines WN 4167 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2026-06-06 through 2026-08-01
Tue,Wed 07:00 Charleston (CHS) 08:10 Chicago Midway (MDW) Southwest Airlines WN 4167 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-06-09 through 2026-07-29
Sun 07:50 Charleston (CHS) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4167 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 08:00 Charleston (CHS) 09:15 Chicago Midway (MDW) Southwest Airlines WN 4167 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 17:55 Charleston (CHS) 19:10 Chicago Midway (MDW) Southwest Airlines WN 4787 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-04 through 2026-08-03
Non-Direct Flights:
Wed,Thu 10:35 Charleston (CHS) 13:45 Chicago Midway (MDW) Southwest Airlines WN 3027 1-stop Boeing 737-700 (73W) 4:10 Valid until 2026-01-01
Mon 07:30 Charleston (CHS) 14:15 Chicago Midway (MDW) Southwest Airlines WN 15 2-stop Boeing 737-700 (Scimitar Winglets) 7:45 Operates only on 2026-01-05
Tue,Wed 14:10 Charleston (CHS) 19:40 Chicago Midway (MDW) Southwest Airlines WN 2390 2-stop Boeing 737-700 (Scimitar Winglets) 6:30 Effective 2026-03-10 through 2026-04-01

A domestic route departing from the Charleston airport (CHS) and arriving at Chicago Midway airport (MDW).
The flight distance is 745 miles, or 1198 km.
The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . 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 2:05 and 2:25.

Return (MDW-CHS) flights

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All airlines flying from Charleston (CHS) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN403

08:15

Charleston (CHS)

09:30

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN947

08:00

Charleston (CHS)

09:15

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN947

18:00

Charleston (CHS)

19:20

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN947

18:55

Charleston (CHS)

20:15

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN947

18:55

Charleston (CHS)

20:15

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1078

06:00

Charleston (CHS)

07:15

Chicago Midway (MDW)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1078

19:30

Charleston (CHS)

20:45

Chicago Midway (MDW)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1078

19:30

Charleston (CHS)

20:45

Chicago Midway (MDW)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1131

07:35

Charleston (CHS)

08:45

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1131

07:35

Charleston (CHS)

08:45

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1131

08:15

Charleston (CHS)

09:20

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:05, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1225

07:10

Charleston (CHS)

08:15

Chicago Midway (MDW)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:05, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1291

16:35

Charleston (CHS)

17:55

Chicago Midway (MDW)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1516

18:30

Charleston (CHS)

19:40

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1516

18:35

Charleston (CHS)

19:45

Chicago Midway (MDW)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1959

19:15

Charleston (CHS)

20:30

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1959

19:20

Charleston (CHS)

20:35

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1959

20:00

Charleston (CHS)

21:15

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1962

18:15

Charleston (CHS)

19:30

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2430

17:15

Charleston (CHS)

18:40

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2430

18:55

Charleston (CHS)

20:20

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2659

19:30

Charleston (CHS)

20:45

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3165

07:15

Charleston (CHS)

08:30

Chicago Midway (MDW)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3165

07:40

Charleston (CHS)

08:55

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3165

07:40

Charleston (CHS)

08:55

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3165

07:40

Charleston (CHS)

08:55

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3165

08:50

Charleston (CHS)

10:05

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3304

17:45

Charleston (CHS)

19:05

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4167

05:30

Charleston (CHS)

06:40

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4167

07:00

Charleston (CHS)

08:10

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4167

07:50

Charleston (CHS)

09:05

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4167

08:00

Charleston (CHS)

09:15

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4787

17:55

Charleston (CHS)

19:10

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3027

10:35

Charleston (CHS)

13:45

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:10, 1-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN15

07:30

Charleston (CHS)

14:15

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2390

14:10

Charleston (CHS)

19:40

Chicago Midway (MDW)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Charleston airport (CHS) and arriving at Chicago Midway airport (MDW).
The flight distance is 745 miles, or 1198 km.
The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . 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 2:05 and 2:25.

Return (MDW-CHS) flights

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