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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 19:55 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 20 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 20min
Updated Jul 13, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 07:45 and 19:55
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 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.

 
Flight
Mon
Aug 10
Tue
Aug 11
Wed
Aug 12
Thu
Aug 13
Fri
Aug 14
Sat
Aug 15
Sun
Aug 16
WN300
----
18:50
18:50
----
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15:20
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WN431
18:10
----
----
18:10
18:10
----
18:10

The timetable & schedule information was updated at 2026-07-13

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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
Aug 12
1 flights(1)
Thursday
Thu
Aug 13
1 flights(1)
Friday
Fri
Aug 14
1 flights(1)
Saturday
Sat
Aug 15
1 flights(1)
Sunday
Sun
Aug 16
1 flights(1)
Monday
Mon
Aug 17
1 flights(1)
Tuesday
Tue
Aug 18
1 flights(1)
Time
Airline
Flight
18:50
Southwest Airlines Southwest Airlines
WN300
18:10
Southwest Airlines Southwest Airlines
WN431
18:10
Southwest Airlines Southwest Airlines
WN431
15:20
Southwest Airlines Southwest Airlines
WN300
18:10
Southwest Airlines Southwest Airlines
WN431
18:10
Southwest Airlines Southwest Airlines
WN431
18:50
Southwest Airlines Southwest Airlines
WN300
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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 20 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)

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 20 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 19:55 depending on the schedule period.

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