All airlines flying from Cancun (CUN) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Mon,Thu,Fri
08:30
Cancun (CUN) 4
12:10
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-03-09 through 2026-04-06 |
| Tue,Wed
08:30
Cancun (CUN) 4
12:10
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-03-10 through 2026-04-01 |
| Sun
09:25
Cancun (CUN) 4
13:05
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-03-08 through 2026-04-05 |
| Fri
09:30
Cancun (CUN) 4
12:10
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-03-06 |
| Sat
09:55
Cancun (CUN) 4
13:40
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-03-14 through 2026-04-04 |
| Sat
10:05
Cancun (CUN) 4
13:40
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-06 through 2026-08-01 |
| Sat
10:55
Cancun (CUN) 4
13:40
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-03-07 |
| Sun
11:25
Cancun (CUN) 4
15:00
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-07 through 2026-08-02 |
| Sun
15:10
Cancun (CUN) 4
18:50
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-05-24 |
| Sat
16:00
Cancun (CUN) 4
19:40
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri,Sun
16:10
Cancun (CUN) 4
19:50
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-04-09 through 2026-05-22 |
| Mon,Thu,Fri,Sun
16:10
Cancun (CUN) 4
19:50
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-05-25 through 2026-06-01 |
| Mon,Thu,Fri
16:10
Cancun (CUN) 4
19:45
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-04 through 2026-08-03 |
| Sat
16:25
Cancun (CUN) 4
19:10
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Valid until 2026-01-03 |
| Sat
18:05
Cancun (CUN) 4
20:45
Chicago Midway (MDW) Southwest Airlines WN 217 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-02-14 through 2026-02-28 |
| Sat
10:50
Cancun (CUN) 4
14:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-04-11 through 2026-05-30 |
| Sat
11:00
Cancun (CUN) 4
13:35
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-02-14 through 2026-02-28 |
| Sat
12:35
Cancun (CUN) 4
16:10
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
12:40
Cancun (CUN) 4
16:15
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-08-04 through 2026-09-30 |
| Sun
12:55
Cancun (CUN) 4
16:40
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-05-24 |
| Mon,Thu,Fri
13:05
Cancun (CUN) 4
16:40
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-08-06 through 2026-09-28 |
| Mon,Thu,Fri
13:20
Cancun (CUN) 4
16:55
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-04 through 2026-08-03 |
| Mon-Wed
13:40
Cancun (CUN) 4
16:25
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-02 through 2026-02-04 |
| Sat
13:40
Cancun (CUN) 4
16:25
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-02-07 |
| Wed
13:40
Cancun (CUN) 4
16:25
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Operates only on 2026-03-04 |
| Mon-Fri
13:45
Cancun (CUN) 4
16:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
13:45
Cancun (CUN) 4
16:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
13:45
Cancun (CUN) 4
16:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-01-26 through 2026-01-30 |
| Tue,Wed,Sun
13:45
Cancun (CUN) 4
16:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
13:45
Cancun (CUN) 4
16:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-02-18 through 2026-03-03 |
| Sat
13:50
Cancun (CUN) 4
16:35
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-01-10 through 2026-01-31 |
| Sun
13:50
Cancun (CUN) 4
17:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-04-12 through 2026-05-17 |
| Sun
13:50
Cancun (CUN) 4
17:30
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-05-31 |
| Mon,Thu,Fri
14:05
Cancun (CUN) 4
17:50
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-03-09 through 2026-04-06 |
| Mon
14:15
Cancun (CUN) 4
17:00
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-01-05 |
| Sat
14:15
Cancun (CUN) 4
17:50
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-06 through 2026-08-01 |
| Sun
14:15
Cancun (CUN) 4
17:50
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-07 through 2026-08-02 |
| Sun
14:25
Cancun (CUN) 4
18:10
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-03-08 through 2026-04-05 |
| Thu,Fri,Sun
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-02-17 through 2026-02-23 |
| Mon
15:00
Cancun (CUN) 4
17:45
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Operates only on 2026-03-02 |
| Sun
15:00
Cancun (CUN) 4
18:35
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-08-09 through 2026-09-27 |
| Thu,Fri
15:05
Cancun (CUN) 4
17:50
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-03-05 through 2026-03-06 |
| Tue,Wed
15:05
Cancun (CUN) 4
18:35
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:30 Effective 2026-06-09 through 2026-07-29 |
| Tue,Wed
15:15
Cancun (CUN) 4
18:55
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
15:40
Cancun (CUN) 4
18:20
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-02-12 through 2026-02-16 |
| Fri
15:40
Cancun (CUN) 4
18:20
Chicago Midway (MDW) Southwest Airlines WN 219 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-02-20 through 2026-02-27 |
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- An international route departing from Cancun airport, Mexico (CUN) and arriving at Chicago Midway 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 3:30 and 4:07.
