Portland (PDX) to Chicago/Midway (MDW) December 2025 Flight Schedule

Flight Portland(PDX) to Midway(MDW)
CHANGE DIRECTION

Portland International Airport Chicago Midway International Airport
PDX : Portland , United States MDW : Chicago , United States
UTC-7(DST) UTC-5(DST)

Portland to Midway Flight Schedule(December 2025)

Flight from Portland(PDX) to Midway(MDW) is operated by 1 airline : Southwest Airlines (WN). You can check flight schedules, flight duration, and aircraft types.

Change Direction(MDW to PDX)

Portland (PDX) to Chicago/Midway (MDW) Flight Schedule

LastUpdate : 2025/09/01 06:15

Flight Schedule on December 2025 , Direct flight departure from Portland with all airlines , flight number, flight duration, aircraft type.

December 2025
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Flight Number / Airline Departure Time Arrival Time Flight Duration Operating Days Aircraft Type Airfare / Tickets
WN4016
Southwest Airlines 		05:00 10:55 3h55m
M------ (Dec 1)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:15 12:10 3h55m
-TWTF-- (Dec 2–5)
737-8-MAX
10:20 16:15 3h55m
-----S- (Dec 6, Dec 13)
737-700 (WL)
06:15 12:10 3h55m
MTWT--- (Dec 8–11)
737-8-MAX
06:30 12:25 3h55m
----F-S (Dec 12, Dec 14)
737-8-MAX
06:15 12:10 3h55m
MTW---- (Dec 15–17)
737-8-MAX
06:30 12:25 3h55m
---T--- (Dec 18)
737-8-MAX
05:00 10:55 3h55m
MT--F-S (Dec 19, Dec 21–23, Dec 26, Dec 28–30)
737-8-MAX
06:15 12:10 3h55m
--WT--- (Dec 24–25, Dec 31)
737-8-MAX
WN4013
Southwest Airlines 		07:45 13:40 3h55m
-----S- (Dec 20, Dec 27)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
Change Direction(MDW to PDX)
Flight schedules as of September 01, 2025, 06:15 AM(OAG data). Schedules may change without notice, so please check with airlines before booking. Refer to FlyTeam's terms of use before proceeding. Some airlines and flight numbers may not be displayed.

FAQ : Portland to Chicago/Midway

How many airlines fly from Portland to Chicago ?
As of December 2025, 1 airline operate direct flights from Portland (PDX) to Chicago/Midway (MDW) : Southwest Airlines.
How far is it from Portland to Chicago?
The distance between Portland (PDX) to Chicago/Midway (MDW) is approximately 1,750 miles(2,810km) by air.
What is the time difference between Portland to Chicago?
The time difference between Portland International Airport(Portland) and Chicago Midway International Airport(Chicago) is +2 hours. Chicago is 2 hours ahead of Portland.Portland is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.Chicago is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.