Southwest Airlines
flight
WN 1999:
Punta Cana - Chicago Midway
Punta Cana - Chicago Midway
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN1999
Effective 2026-04-11 through 2026-05-30
Mon
-
-
Tue
-
-
Wed
-
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Thu
-
-
Fri
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-
Sat
Sun
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-
Duration: 5:00, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-03-10 through 2026-04-01
Mon
-
-
Tue
Wed
Thu
-
-
Fri
-
-
Sat
-
-
Sun
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-
Duration: 5:05, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-03-09 through 2026-04-06
Mon
Tue
-
-
Wed
-
-
Thu
Fri
Sat
-
-
Sun
-
-
Duration: 5:10, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
-
Wed
-
-
Thu
Fri
Sat
-
-
Sun
-
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-06-09 through 2026-07-29
Mon
-
-
Tue
Wed
Thu
-
-
Fri
-
-
Sat
-
-
Sun
-
-
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-03-14 through 2026-04-04
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
Sun
-
-
Duration: 5:10, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-06-06 through 2026-08-01
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
Sun
-
-
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-01-10 through 2026-02-07
Mon
-
-
Tue
-
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Wed
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-
Thu
-
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Fri
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-
Sat
Sun
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-
Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Operates only on 2026-01-03
Mon
-
-
Tue
-
-
Wed
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-
Thu
-
-
Fri
-
-
Sat
Sun
-
-
Duration: 5:00, non-stop
Boeing 737-700 (Scimitar Winglets)
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-03-08 through 2026-04-05
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
-
-
Sun
Duration: 5:10, non-stop
Boeing 737-700 (Scimitar Winglets)
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-06-07 through 2026-08-02
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
-
-
Sun
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-02-14 through 2026-02-28
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
Sun
-
-
Duration: 5:00, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Effective 2026-03-05 through 2026-03-06
Mon
-
-
Tue
-
-
Wed
-
-
Thu
Fri
Sat
-
-
Sun
-
-
Duration: 5:10, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN1999
Operates only on 2026-03-07
Mon
-
-
Tue
-
-
Wed
-
-
Thu
-
-
Fri
-
-
Sat
Sun
-
-
Duration: 5:10, non-stop
Boeing 737 MAX 8 (7M8)
Boeing 737 MAX 8 (7M8)
- WN 1999 is an international flight departing from Punta Cana airport, Dominican Republic (PUJ) and arriving at Chicago Midway airport, United States (MDW).
- The flight distance is 1966 miles, or 3164 km.
- The timezone of the departure airport is UTC-4 , 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 4:45 and 5:10.