Southwest Airlines flights from Midway, Chicago (MDW) to Cancun (CUN).

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FLIGHT SCHEDULE
Direct Flights:
Sun 08:05 Midway, Chicago (MDW) 11:45 Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-10-05 through 2025-10-26
Sat 08:20 Midway, Chicago (MDW) 12:00 Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-10-04 through 2025-11-01
Sat 06:10 Midway, Chicago (MDW) 10:55 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-22 through 2025-11-29
Sat 06:10 Midway, Chicago (MDW) 10:55 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-12-20 through 2026-01-03
Sat 06:35 Midway, Chicago (MDW) 11:20 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-08 through 2025-11-15
Sat 06:35 Midway, Chicago (MDW) 11:20 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-06 through 2025-12-13
Mon-Fri 09:55 Midway, Chicago (MDW) 13:30 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-08-05 through 2025-10-01
Sun 10:35 Midway, Chicago (MDW) 14:10 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-08-10 through 2025-09-28
Sat 12:25 Midway, Chicago (MDW) 16:00 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-06-07 through 2025-08-02
Tue,Wed 16:30 Midway, Chicago (MDW) 20:05 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 16:35 Midway, Chicago (MDW) 20:10 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 16:35 Midway, Chicago (MDW) 20:10 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-07-07 through 2025-08-01
Sun 17:25 Midway, Chicago (MDW) 21:00 Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-06-08 through 2025-08-03
Sun 08:30 Midway, Chicago (MDW) 12:10 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (73W) 3:40 Valid until 2025-06-01
Sat 08:30 Midway, Chicago (MDW) 12:10 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Valid until 2025-05-31
Sun 08:45 Midway, Chicago (MDW) 13:30 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Operates only on 2025-11-30
Tue,Wed 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-17 through 2025-11-20
Mon-Wed 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-25 through 2025-12-01
Tue-Thu 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-27 through 2025-12-04
Mon-Fri 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-05 through 2025-12-11
Mon-Wed 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-15 through 2025-12-17
Mon,Tue,Fri,Sun 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-12-19 through 2026-01-04
Wed,Thu 09:05 Midway, Chicago (MDW) 13:50 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-24 through 2026-01-01
Mon-Fri 09:35 Midway, Chicago (MDW) 13:10 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Valid until 2025-06-04
Mon,Thu,Fri,Sun 10:40 Midway, Chicago (MDW) 15:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 10:40 Midway, Chicago (MDW) 15:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-21 through 2025-11-28
Fri,Sun 10:40 Midway, Chicago (MDW) 15:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-12-07 through 2025-12-14
Thu 10:40 Midway, Chicago (MDW) 15:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2025-12-18
Mon 10:40 Midway, Chicago (MDW) 15:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-01-05
Sat 15:40 Midway, Chicago (MDW) 20:25 Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-08 through 2026-01-03
Sat,Sun 06:20 Midway, Chicago (MDW) 09:55 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-06-07 through 2025-08-03
Mon-Fri 09:00 Midway, Chicago (MDW) 12:40 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (73W) 3:40 Effective 2025-06-05 through 2025-08-04
Sat 09:15 Midway, Chicago (MDW) 12:50 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-08-09 through 2025-09-27
Mon-Fri 09:40 Midway, Chicago (MDW) 13:15 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-02 through 2025-10-31
Sat 09:40 Midway, Chicago (MDW) 13:15 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-10-04 through 2025-11-01
Sun 10:40 Midway, Chicago (MDW) 14:15 Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-05 through 2025-10-26
Sat 10:25 Midway, Chicago (MDW) 14:00 Cancun (CUN) 4 Southwest Airlines WN 230 Non-stop Boeing 737-700 (73W) 3:35 Valid until 2025-05-31
Sun 10:45 Midway, Chicago (MDW) 14:25 Cancun (CUN) 4 Southwest Airlines WN 230 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Valid until 2025-06-01

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Parallax here MDW-CUN

An international route departing from Midway, Chicago airport, United States (MDW) and arriving at Cancun airport, Mexico (CUN).
The flight distance is 1434 miles, or 2307 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 3:35 and 3:45.

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Southwest Airlines flights from Midway, Chicago (MDW) to Cancun (CUN).

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN216

08:05

Midway, Chicago (MDW)

11:45

Cancun (CUN) 4

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN216

08:20

Midway, Chicago (MDW)

12:00

Cancun (CUN) 4

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN218

06:10

Midway, Chicago (MDW)

10:55

Cancun (CUN) 4

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN218

06:10

Midway, Chicago (MDW)

10:55

Cancun (CUN) 4

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN218

06:35

Midway, Chicago (MDW)

11:20

Cancun (CUN) 4

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN218

06:35

Midway, Chicago (MDW)

11:20

Cancun (CUN) 4

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN218

09:55

Midway, Chicago (MDW)

13:30

Cancun (CUN) 4

Effective 2025-08-05 through 2025-10-01

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN218

10:35

Midway, Chicago (MDW)

14:10

Cancun (CUN) 4

Effective 2025-08-10 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN218

12:25

Midway, Chicago (MDW)

16:00

Cancun (CUN) 4

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN218

16:30

Midway, Chicago (MDW)

20:05

Cancun (CUN) 4

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN218

16:35

Midway, Chicago (MDW)

20:10

Cancun (CUN) 4

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN218

16:35

Midway, Chicago (MDW)

20:10

Cancun (CUN) 4

Effective 2025-07-07 through 2025-08-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN218

17:25

Midway, Chicago (MDW)

21:00

Cancun (CUN) 4

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN220

08:30

Midway, Chicago (MDW)

12:10

Cancun (CUN) 4

Valid until 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:40, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN220

08:30

Midway, Chicago (MDW)

12:10

Cancun (CUN) 4

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

08:45

Midway, Chicago (MDW)

13:30

Cancun (CUN) 4

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-11-27 through 2025-12-04

Mon
-

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-12-05 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

09:05

Midway, Chicago (MDW)

13:50

Cancun (CUN) 4

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN220

09:35

Midway, Chicago (MDW)

13:10

Cancun (CUN) 4

Valid until 2025-06-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

10:40

Midway, Chicago (MDW)

15:25

Cancun (CUN) 4

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

10:40

Midway, Chicago (MDW)

15:25

Cancun (CUN) 4

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

10:40

Midway, Chicago (MDW)

15:25

Cancun (CUN) 4

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

10:40

Midway, Chicago (MDW)

15:25

Cancun (CUN) 4

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

10:40

Midway, Chicago (MDW)

15:25

Cancun (CUN) 4

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN220

15:40

Midway, Chicago (MDW)

20:25

Cancun (CUN) 4

Effective 2025-11-08 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN228

06:20

Midway, Chicago (MDW)

09:55

Cancun (CUN) 4

Effective 2025-06-07 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN228

09:00

Midway, Chicago (MDW)

12:40

Cancun (CUN) 4

Effective 2025-06-05 through 2025-08-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:40, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN228

09:15

Midway, Chicago (MDW)

12:50

Cancun (CUN) 4

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN228

09:40

Midway, Chicago (MDW)

13:15

Cancun (CUN) 4

Effective 2025-10-02 through 2025-10-31

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN228

09:40

Midway, Chicago (MDW)

13:15

Cancun (CUN) 4

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN228

10:40

Midway, Chicago (MDW)

14:15

Cancun (CUN) 4

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN230

10:25

Midway, Chicago (MDW)

14:00

Cancun (CUN) 4

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN230

10:45

Midway, Chicago (MDW)

14:25

Cancun (CUN) 4

Valid until 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:40, non-stop
Boeing 737 MAX 8 (7M8)

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Parallax here MDW-CUN

An international route departing from Midway, Chicago airport, United States (MDW) and arriving at Cancun airport, Mexico (CUN).
The flight distance is 1434 miles, or 2307 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 3:35 and 3:45.

All MDW-CUN flights

All Southwest Airlines flights

Return (CUN-MDW) flights

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