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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 18:55 depending on the schedule period. The flight distance is 898 miles (1445 km). Flight time ranges from 2 hours and 35 minutes to 2 hours and 40 minutes.

PWM
Portland Jetport
USAPortland , USA
MDW
Chicago Midway
USAChicago , USA
PWM
Portland Jetport
USAPortland , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 2h 35min to 2h 40min
Updated Oct 5, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 06:30 and 18:55
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7 flights/week
7 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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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.

 
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The timetable & schedule information was updated at

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Portland to Chicago scheduled departures

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

Friday
Fri
Nov 06
0 flights(0)
Saturday
Sat
Nov 07
0 flights(0)
Sunday
Sun
Nov 08
0 flights(0)
Monday
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Nov 09
0 flights(0)
Tuesday
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Nov 10
0 flights(0)
Wednesday
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Nov 11
0 flights(0)
Thursday
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Nov 12
0 flights(0)
Time
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Flight
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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 35 minutes to 2 hours and 40 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737-800 (winglets) Passenger/BBJ2, Boeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)

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 35 minutes to 2 hours and 40 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 18:55 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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