MDW → PWMChicago to Portland

live

Direct flights from Chicago (MDW) to Portland (PWM): 6 nonstop departures observed each week across 1 airline. 83% of the last 6 tracked flights arrived within 15 minutes of schedule. The median arrival is 8 minutes early. No cancellations were recorded across the 7 tracked flights. The nonstop covers 1,437 km, an estimated 2 hours 21 minutes in the air. Measured by Pro Flight Search from live flight boards at Chicago and Portland. Updated 1 November 2026 at 04:53 UTC.

MDW Chicago smooth · +2
PWM Portland smooth · +0
1,437 km · ~2h 21m est.
dep bank 07:45–19:506x weekly
Runs reliable · 1 airline · 6x weekly · nonstop
83% on time

of the last 6 tracked MDW → PWM flights arrived within 15 minutes

Median arrival delay is −8 min. 0 of 7 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−8 minacross the last 6 arrivals
Flight time~2h 21mestimated from route distance
Weekly departures6x1 direct airline on the leg

The week

scheduled departures · origin local time
06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines

Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.

Who flies it

observed on the boards · 7 days
Southwest AirlinesWN100% on time

Flights WN2775 07:45 Tu We · WN2398 18:40 Mo Th Fr · WN2746 19:50 Su

History

operated legs · board outcomes
10-30WN2398dep +5 → arr−8
10-29JRE751arrived+43
10-29WN2398dep −5 → arr−16
10-28WN2775dep −10 → arr−19
10-27WN2775departed−11
10-26WN2398dep +3 → arr−8
10-25WN2746dep +25 → arr+13

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
MDWChicago +2 min smooth 🌤 overcast · E 4 kt Full MDW delay board →
PWMPortland +0 min smooth 🌤 few clouds · W 10 kt Full PWM delay board →

Weather lens

Conditions are tightest at MDW: a 36% chance of a 15+ minute delay. In this weather, the more delayed of the two airports is typically about +7 min. Both figures come from the two airports' delay records in similar weather. See live delays → · Weather risk by airport →

How the Chicago to Portland route actually runs

Pro Flight Search records official board updates for nonstop MDW to PWM flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.

Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure

Cite this data

Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.

Suggested citation

Pro Flight Search: Chicago (MDW) to Portland (PWM) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/MDW-PWM
How we measure this →

MDW to PWM questions

Is MDW–PWM running on time right now?

Smooth skies ahead. Both endpoints currently score the same, route health score 100/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on MDW–PWM?

Operators schedule morning departures around 07:45 and evening departures around 18:40 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the PWM delay card to confirm conditions when you'd arrive.

How long is the flight from MDW to PWM?

Great-circle distance is 1,437 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 131–153 min gate-to-gate on this route.

How often does MDW–PWM fly?

Southwest Airlines runs the route with about 6 flights a week (sun, mon, tue, wed, thu, fri). Since one carrier owns the route, a single disruption tends to ripple through the day.