All airlines flying from Chicago Midway (MDW) to Cancun (CUN).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sun
09:40
Chicago Midway (MDW)
13:15
Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
09:55
Chicago Midway (MDW)
13:30
Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
10:05
Chicago Midway (MDW)
13:40
Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-09 through 2026-07-29 |
| Sat
10:25
Chicago Midway (MDW)
14:00
Cancun (CUN) 4 Southwest Airlines WN 216 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-06 through 2026-08-01 |
| Sat
05:55
Chicago Midway (MDW)
10:40
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Valid until 2026-01-03 |
| Mon,Thu,Fri
08:25
Chicago Midway (MDW)
12:00
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-08-06 through 2026-09-28 |
| Tue,Wed
08:35
Chicago Midway (MDW)
12:10
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-08-04 through 2026-09-30 |
| Sat
08:40
Chicago Midway (MDW)
12:15
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-08-08 through 2026-09-26 |
| Sun
08:40
Chicago Midway (MDW)
12:15
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
09:35
Chicago Midway (MDW)
13:10
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
10:30
Chicago Midway (MDW)
14:00
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737-700 (Scimitar Winglets) 3:30 Effective 2026-04-07 through 2026-06-03 |
| Sat
10:40
Chicago Midway (MDW)
14:10
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:30 Effective 2026-04-11 through 2026-05-30 |
| Sun
11:00
Chicago Midway (MDW)
14:35
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-04-12 through 2026-05-31 |
| Sat
13:25
Chicago Midway (MDW)
18:00
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Operates only on 2026-03-07 |
| Sat
13:25
Chicago Midway (MDW)
17:00
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-03-14 through 2026-04-04 |
| Thu,Fri
16:05
Chicago Midway (MDW)
20:45
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-03-05 through 2026-03-06 |
| Mon,Thu,Fri
16:05
Chicago Midway (MDW)
19:45
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-03-09 through 2026-04-06 |
| Sun
16:35
Chicago Midway (MDW)
20:15
Cancun (CUN) 4 Southwest Airlines WN 218 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-03-08 through 2026-04-05 |
| Mon,Tue,Fri,Sun
08:35
Chicago Midway (MDW)
13:20
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Valid until 2026-01-04 |
| Wed,Thu
08:40
Chicago Midway (MDW)
13:25
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (73W) 3:45 Valid until 2026-01-01 |
| Mon-Fri
09:15
Chicago Midway (MDW)
13:55
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
09:15
Chicago Midway (MDW)
13:55
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
09:15
Chicago Midway (MDW)
13:55
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
09:15
Chicago Midway (MDW)
13:55
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
09:15
Chicago Midway (MDW)
13:55
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-02-18 through 2026-03-04 |
| Sat
09:20
Chicago Midway (MDW)
14:00
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-01-10 through 2026-02-07 |
| Thu,Fri,Sun
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-17 through 2026-02-23 |
| Mon
10:35
Chicago Midway (MDW)
15:15
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-03-02 |
| Mon
10:40
Chicago Midway (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 |
| Mon,Thu,Fri
10:45
Chicago Midway (MDW)
15:25
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
10:45
Chicago Midway (MDW)
15:25
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-20 through 2026-03-01 |
| Sat
11:45
Chicago Midway (MDW)
16:25
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-02-14 through 2026-02-28 |
| Sat
15:40
Chicago Midway (MDW)
20:25
Cancun (CUN) 4 Southwest Airlines WN 220 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Operates only on 2026-01-03 |
| Sat
05:30
Chicago Midway (MDW)
10:15
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-02-14 through 2026-02-28 |
| Sat
06:10
Chicago Midway (MDW)
09:45
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-04-11 through 2026-05-30 |
| Sun
06:20
Chicago Midway (MDW)
10:05
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
06:25
Chicago Midway (MDW)
10:00
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-04 through 2026-08-03 |
| Sat,Sun
07:30
Chicago Midway (MDW)
11:05
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Effective 2026-06-06 through 2026-08-02 |
| Sat
07:50
Chicago Midway (MDW)
12:30
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Operates only on 2026-03-07 |
| Sat
07:50
Chicago Midway (MDW)
11:30
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-03-14 through 2026-04-04 |
| Thu,Fri
08:05
Chicago Midway (MDW)
12:50
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-03-05 through 2026-03-06 |
| Mon,Thu,Fri
08:05
Chicago Midway (MDW)
11:50
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-03-09 through 2026-04-06 |
| Tue,Wed
08:05
Chicago Midway (MDW)
11:50
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-03-10 through 2026-04-01 |
| Sun
08:30
Chicago Midway (MDW)
12:10
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-04-12 through 2026-05-17 |
| Sun
08:30
Chicago Midway (MDW)
12:10
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-05-31 |
| Sun
09:15
Chicago Midway (MDW)
12:50
Cancun (CUN) 4 Southwest Airlines WN 228 Non-stop Boeing 737 MAX 8 (7M8) 3:35 Operates only on 2026-05-24 |
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- An international route departing from Chicago Midway 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 3:30 and 4:02.
