Portland (PDX) to Chicago/Midway (MDW) June 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(June 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 June 2025 , Direct flight departure from Portland with all airlines , flight number, flight duration, aircraft type.

June 2025
  • Southwest Airlines [ Show / Hide ]
Flight Number / Airline Departure Time Arrival Time Flight Duration Operating Days Aircraft Type Airfare / Tickets
WN407
Southwest Airlines
05:30 11:30 4h0m
M------ (Jun 2)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:15 12:15 4h0m
-TW---- (Jun 3–4)
737-700 (WL)
WN2735
Southwest Airlines
05:50 11:45 3h55m
---TF-- (Jun 5–6)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:20 12:15 3h55m
-----S- (Jun 7, Jun 14, Jun 21, Jun 28)
737-8-MAX
05:50 11:45 3h55m
M--TF-- (Jun 9, Jun 12–13, Jun 16, Jun 19–20, Jun 23, Jun 26–27)
737-700 (WL)
08:55 14:50 3h55m
-TW---- (Jun 10–11, Jun 17–18, Jun 24–25)
737-700 (WL)
05:50 11:45 3h55m
M------ (Jun 30)
737-700 (WL)
WN2321
Southwest Airlines
06:05 12:00 3h55m
-TW---S (Jun 8, Jun 10–11, Jun 15, Jun 17–18, Jun 22, Jun 24–25, Jun 29)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN4169
Southwest Airlines
08:30 14:25 3h55m
---TF-- (Jun 5–6)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
09:20 15:15 3h55m
-----S- (Jun 7, Jun 14, Jun 21, Jun 28)
737-700 (WL)
08:30 14:25 3h55m
M--TF-- (Jun 9, Jun 12–13, Jun 16, Jun 19–20, Jun 23, Jun 26–27, Jun 30)
737-700 (WL)
WN1895
Southwest Airlines
08:30 21:15 10h45m
3 Transfers
------S (Jun 8, Jun 15, Jun 22, Jun 29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN4170
Southwest Airlines
14:30 20:25 3h55m
---TF-- (Jun 5–6)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
14:30 20:25 3h55m
-----S- (Jun 7, Jun 14, Jun 21, Jun 28)
737-700 (WL)
13:55 19:50 3h55m
------S (Jun 8, Jun 15, Jun 22, Jun 29)
737-800 (WL)
14:30 20:25 3h55m
MTWTF-- (Jun 9–13, Jun 16–20, Jun 23–27, Jun 30)
737-8-MAX
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 June 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.