All airlines flying from Cancun (CUN) to Midway, Chicago (MDW).

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FLIGHT SCHEDULE
Direct Flights:
Daily 08:30 Cancun (CUN) 4 12:05 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (73W) 3:35 Effective 2025-06-05 through 2025-08-04
Sat 11:55 Cancun (CUN) 4 14:45 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2025-11-08 through 2025-11-15
Sat 11:55 Cancun (CUN) 4 14:45 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2025-12-06 through 2025-12-13
Sat 12:00 Cancun (CUN) 4 15:35 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-10-04 through 2025-11-01
Sun 12:05 Cancun (CUN) 4 15:40 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-05 through 2025-10-26
Sat 14:25 Cancun (CUN) 4 18:05 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-08-09 through 2025-09-27
Sun 15:00 Cancun (CUN) 4 18:40 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (73W) 3:40 Operates only on 2025-08-31
Mon-Fri 15:10 Cancun (CUN) 4 18:50 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (73W) 3:40 Effective 2025-08-05 through 2025-10-01
Sun 15:50 Cancun (CUN) 4 19:30 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (73W) 3:40 Effective 2025-08-10 through 2025-08-24
Sun 15:50 Cancun (CUN) 4 19:30 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (73W) 3:40 Effective 2025-09-07 through 2025-09-28
Sat 16:05 Cancun (CUN) 4 19:45 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Valid until 2025-05-31
Sun 16:10 Cancun (CUN) 4 19:50 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Valid until 2025-06-01
Sat 16:25 Cancun (CUN) 4 19:10 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-22 through 2025-11-29
Sat 16:25 Cancun (CUN) 4 19:10 Midway, Chicago (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-12-20 through 2026-01-03
Thu,Sun 08:20 Cancun (CUN) 4 11:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-11-27 through 2025-11-30
Mon-Fri,Sun 09:00 Cancun (CUN) 4 12:40 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (73W) 3:40 Valid until 2025-05-02
Daily 09:00 Cancun (CUN) 4 12:40 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (73W) 3:40 Effective 2025-05-03 through 2025-06-04
Sun 13:00 Cancun (CUN) 4 16:40 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-06-08 through 2025-08-03
Sat 14:00 Cancun (CUN) 4 17:45 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-10-04 through 2025-11-01
Sun 14:15 Cancun (CUN) 4 18:05 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:50 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri,Sun 14:15 Cancun (CUN) 4 17:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 14:15 Cancun (CUN) 4 17:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-11-21 through 2025-11-28
Fri,Sun 14:15 Cancun (CUN) 4 17:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2025-12-07 through 2025-12-14
Thu 14:15 Cancun (CUN) 4 17:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2025-12-18
Mon 14:15 Cancun (CUN) 4 17:00 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-01-05
Sat 15:05 Cancun (CUN) 4 18:45 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-06-07 through 2025-08-02
Sat 15:10 Cancun (CUN) 4 17:55 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-08 through 2025-11-15
Sat 15:10 Cancun (CUN) 4 17:55 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-06 through 2025-12-13
Tue,Wed 15:15 Cancun (CUN) 4 18:50 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-07 through 2025-10-29
Mon-Fri 15:20 Cancun (CUN) 4 18:55 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-06-05 through 2025-07-03
Mon-Fri 15:20 Cancun (CUN) 4 18:55 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2025-07-07 through 2025-08-04
Mon,Thu,Fri 15:20 Cancun (CUN) 4 18:55 Midway, Chicago (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-02 through 2025-10-31
Tue,Wed 13:45 Cancun (CUN) 4 16:30 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 13:45 Cancun (CUN) 4 16:30 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-17 through 2025-11-20
Mon-Fri 13:45 Cancun (CUN) 4 16:30 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-02 through 2025-12-11
Mon-Wed 13:45 Cancun (CUN) 4 16:30 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-15 through 2025-12-17
Wed,Thu 13:45 Cancun (CUN) 4 16:30 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-24 through 2026-01-01
Mon-Wed 14:30 Cancun (CUN) 4 17:15 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 14:30 Cancun (CUN) 4 17:15 Midway, Chicago (MDW) Southwest Airlines WN 221 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-19 through 2026-01-04
Sat 11:20 Cancun (CUN) 4 14:00 Midway, Chicago (MDW) Southwest Airlines WN 229 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-11-22 through 2025-11-29
Sat 11:20 Cancun (CUN) 4 14:00 Midway, Chicago (MDW) Southwest Airlines WN 229 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2025-12-20 through 2026-01-03

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Parallax here CUN-MDW

An international route departing from Cancun airport, Mexico (CUN) and arriving at Midway, Chicago airport, United States (MDW).
The flight distance is 1434 miles, or 2307 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 3:35 and 3:50.

Return (MDW-CUN) flights

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All airlines flying from Cancun (CUN) to Midway, Chicago (MDW).

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN217

08:30

Cancun (CUN) 4

12:05

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

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

Southwest Airlines WN217

11:55

Cancun (CUN) 4

14:45

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN217

11:55

Cancun (CUN) 4

14:45

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN217

12:00

Cancun (CUN) 4

15:35

Midway, Chicago (MDW)

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 WN217

12:05

Cancun (CUN) 4

15:40

Midway, Chicago (MDW)

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 WN217

14:25

Cancun (CUN) 4

18:05

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN217

15:00

Cancun (CUN) 4

18:40

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN217

15:10

Cancun (CUN) 4

18:50

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN217

15:50

Cancun (CUN) 4

19:30

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN217

15:50

Cancun (CUN) 4

19:30

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN217

16:05

Cancun (CUN) 4

19:45

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN217

16:10

Cancun (CUN) 4

19:50

Midway, Chicago (MDW)

Valid until 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN217

16:25

Cancun (CUN) 4

19:10

Midway, Chicago (MDW)

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 WN217

16:25

Cancun (CUN) 4

19:10

Midway, Chicago (MDW)

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 WN219

08:20

Cancun (CUN) 4

11:00

Midway, Chicago (MDW)

Effective 2025-11-27 through 2025-11-30

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun

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

Southwest Airlines WN219

09:00

Cancun (CUN) 4

12:40

Midway, Chicago (MDW)

Valid until 2025-05-02

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN219

09:00

Cancun (CUN) 4

12:40

Midway, Chicago (MDW)

Effective 2025-05-03 through 2025-06-04

Mon

Tue

Wed

Thu

Fri

Sat

Sun

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

Southwest Airlines WN219

13:00

Cancun (CUN) 4

16:40

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN219

14:00

Cancun (CUN) 4

17:45

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN219

14:15

Cancun (CUN) 4

18:05

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:50, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN219

14:15

Cancun (CUN) 4

17:00

Midway, Chicago (MDW)

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 WN219

14:15

Cancun (CUN) 4

17:00

Midway, Chicago (MDW)

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 WN219

14:15

Cancun (CUN) 4

17:00

Midway, Chicago (MDW)

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 WN219

14:15

Cancun (CUN) 4

17:00

Midway, Chicago (MDW)

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 WN219

14:15

Cancun (CUN) 4

17:00

Midway, Chicago (MDW)

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 WN219

15:05

Cancun (CUN) 4

18:45

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN219

15:10

Cancun (CUN) 4

17:55

Midway, Chicago (MDW)

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 WN219

15:10

Cancun (CUN) 4

17:55

Midway, Chicago (MDW)

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 WN219

15:15

Cancun (CUN) 4

18:50

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN219

15:20

Cancun (CUN) 4

18:55

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN219

15:20

Cancun (CUN) 4

18:55

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN219

15:20

Cancun (CUN) 4

18:55

Midway, Chicago (MDW)

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 WN221

13:45

Cancun (CUN) 4

16:30

Midway, Chicago (MDW)

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 WN221

13:45

Cancun (CUN) 4

16:30

Midway, Chicago (MDW)

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 WN221

13:45

Cancun (CUN) 4

16:30

Midway, Chicago (MDW)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN221

13:45

Cancun (CUN) 4

16:30

Midway, Chicago (MDW)

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 WN221

13:45

Cancun (CUN) 4

16:30

Midway, Chicago (MDW)

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 WN221

14:30

Cancun (CUN) 4

17:15

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN221

14:30

Cancun (CUN) 4

17:15

Midway, Chicago (MDW)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN229

11:20

Cancun (CUN) 4

14:00

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN229

11:20

Cancun (CUN) 4

14:00

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

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Parallax here CUN-MDW

An international route departing from Cancun airport, Mexico (CUN) and arriving at Midway, Chicago airport, United States (MDW).
The flight distance is 1434 miles, or 2307 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 3:35 and 3:50.

Return (MDW-CUN) flights

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