Airlines with flights from Chicago to Punta Cana
There are three airlines with scheduled flights between MDW and PUJ. Southwest is the only airline with non-stop flights from Midway International Airport to Punta Cana International Airport and the flight time is 4 hours and 30 minutes.
There are three airlines with scheduled flights between MDW and PUJ. Southwest is the only airline with non-stop flights from Midway International Airport to Punta Cana International Airport and the flight time is 4 hours and 30 minutes. Choose airline
Direct
Non-stop
4h 30min
Via Orlando
6h 5min
Via Nashville
6h 5min
Via Atlanta
6h 20min
Via Baltimore
6h 25min
Via Atlanta
6h 54min
Via Saint Louis
6h 55min
Schedules
Non-stop with Southwest Airlines
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Total flight time: 4 hours and 30 minutes
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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7 flights per week
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Boeing 737MAX 8 Passenger
MDW
Direct
PUJ
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2682
10:30
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The timetable & schedule information was updated at 2026-04-21
Via Orlando with Southwest Airlines
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Total flight time: 6h 05m - 8h 00m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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40 flights per week
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Boeing 737MAX 8 Passenger
MDW
Via MCO
PUJ
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN801
WN782
WN782
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05:00
05:00
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WN2758
WN782
WN782
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06:15
06:15
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05:00
05:10
WN2815
WN782
WN782
05:10
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WN2816
WN782
WN782
06:30
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The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
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Total flight time: 6h 05m - 8h 10m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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6 flights per week
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Boeing 737MAX 8 Passenger
MDW
Via BNA
PUJ
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
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Total flight time: 6h 20m - 8h 59m.
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Sky Team Alliance
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25 flights per week
MDW
Via ATL
PUJ
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL1285
DL1796
DL1796
06:05
06:05
06:05
06:05
06:05
06:05
06:05
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
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Total flight time: 6h 25m - 9h 55m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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19 flights per week
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Boeing 737MAX 8 Passenger
MDW
Via BWI
PUJ
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2687
WN811
WN811
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05:00
WN2742
WN821
WN821
07:00
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The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Frontier