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Direct flights from Chicago to Portland

Airlines Schedules

MDW - PWM route map All flights from MDW to PWM non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Portland International Jetport (PWM), Maine, USA with Southwest Airlines. 7 weekly departures are currently scheduled on this route. Departure times range from 07:45 to 20:00 depending on the schedule period. The flight distance is 898 miles (1445 km). Flight time ranges from 2 hours and 10 minutes to 2 hours and 25 minutes.

MDW
Chicago Midway
USAChicago , USA
PWM
Portland Jetport
USAPortland , USA
MDW
Chicago Midway
USAChicago , USA
Portland Jetport
USAPortland , USA
PWM
Flight time 2h 10min to 2h 25min
Updated Oct 5, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 07:45 and 20:00
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7 flights/week
7 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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Flight schedule from Chicago to Portland 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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Chicago to Portland scheduled departures

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

Wednesday
Wed
Nov 04
0 flights(0)
Thursday
Thu
Nov 05
0 flights(0)
Friday
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Nov 06
0 flights(0)
Saturday
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Nov 07
0 flights(0)
Sunday
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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)
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MDW-PWM flight route
Route map from Chicago, MDW to Portland, PWM. The distance is 898 miles or 1445 km.
Chicago - Portland direct flight map
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MDW - PWM route facts

  • Distance
    898 miles (1445 km)
  • Flight time
    2 hours and 10 minutes to 2 hours and 25 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737MAX 8 Passenger and Boeing 737-800 (winglets) Passenger/BBJ2

Route FAQ

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

Scheduled flight time from MDW to PWM ranges from 2 hours and 10 minutes to 2 hours and 25 minutes. The route covers 898 miles (1445 km).

7 weekly departures are currently scheduled on this route, with published departure times ranging from 07:45 to 20:00 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
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