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Direct flights from Portland to Chicago

Airlines Schedules

PWM - MDW route map All flights from PWM to MDW non-stop. There are direct flights from Portland International Jetport (PWM), Maine, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 7 weekly departures are currently scheduled on this route. Departure times range from 06:30 to 18:00 depending on the schedule period. The flight distance is 898 miles (1445 km). Flight time ranges from 2 hours and 30 minutes to 2 hours and 35 minutes.

PWM
Portland Jetport
USAPortland , USA
MDW
Chicago Midway
USAChicago , USA
PWM
Portland Jetport
USAPortland , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 2h 30min to 2h 35min
Updated Aug 24, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 06:30 and 18:00
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
7 flights/week
7 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Portland to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Sep 21
Tue
Sep 22
Wed
Sep 23
Thu
Sep 24
Fri
Sep 25
Sat
Sep 26
Sun
Sep 27
WN3338
07:40
07:45
07:45
07:40
07:40
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07:40
WN2751
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15:45
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The timetable & schedule information was updated at 2026-08-24

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Portland to Chicago scheduled departures

Select a date to see every published non-stop departure between PWM and MDW.

Sunday
Sun
Sep 20
1 flights(1)
Monday
Mon
Sep 21
1 flights(1)
Tuesday
Tue
Sep 22
1 flights(1)
Wednesday
Wed
Sep 23
1 flights(1)
Thursday
Thu
Sep 24
1 flights(1)
Friday
Fri
Sep 25
1 flights(1)
Saturday
Sat
Sep 26
1 flights(1)
Time
Airline
Flight
07:40
Southwest Airlines Southwest Airlines
WN3338
07:40
Southwest Airlines Southwest Airlines
WN3338
07:45
Southwest Airlines Southwest Airlines
WN3338
07:45
Southwest Airlines Southwest Airlines
WN3338
07:40
Southwest Airlines Southwest Airlines
WN3338
07:40
Southwest Airlines Southwest Airlines
WN3338
15:45
Southwest Airlines Southwest Airlines
WN2751
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PWM-MDW flight route
Route map from Portland, PWM to Chicago, MDW. The distance is 898 miles or 1445 km.
Portland - Chicago direct flight map
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PWM - MDW route facts

  • Distance
    898 miles (1445 km)
  • Flight time
    2 hours and 30 minutes to 2 hours and 35 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737-800 (winglets) Passenger/BBJ2, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737MAX 8 Passenger

Route FAQ

Southwest Airlines operates non-stop flights from PWM to MDW with 7 weekly departures.

Scheduled flight time from PWM to MDW ranges from 2 hours and 30 minutes to 2 hours and 35 minutes. The route covers 898 miles (1445 km).

7 weekly departures are currently scheduled on this route, with published departure times ranging from 06:30 to 18:00 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
Direct flights from Portland to IL, USA
From Portland to Chicago

ORD Chicago O Hare International
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