PWM → MDWPortland to Chicago

live

Direct flights from Portland (PWM) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 57% of the last 7 operated flights arrived within 15 minutes of schedule. The median arrival is 11 minutes late. 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 Portland and Chicago. Updated 16 October 2026 at 08:10 UTC.

Today, PWM → MDW

Fri 16 Oct · local times
  1. · WN2876Southwest Airlines On schedule MDW 08:05scheduled

Checked PWM board 22:48 · MDW board 03:10

PWM Portland smooth · +4
MDW Chicago heavy · +30
1,437 km · ~2h 21m est.
dep bank 06:30–18:007x weekly
Runs rough · 1 airline · 7x weekly · nonstop
57% on time

of the last 7 operated PWM → MDW flights arrived within 15 minutes

Median arrival delay is +11 min. 0 of 7 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival+11 minacross the last 7 operated legs
Flight time~2h 21mestimated from route distance
Weekly departures7x1 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 AirlinesWN57% on time

Flights WN2876 06:30 Mo Th Fr · WN3550 07:25 Su · WN3557 16:35 Sa · WN1881 18:00 Tu We

History

operated legs · board outcomes
10-15WN2876dep +10 → arr−6
10-14WN1881dep +47 → arr+37
10-13WN1881dep +29 → arr+11
10-12WN2876dep +10 → arr−15
10-11WN3550dep +11 → arr−11
10-10WN3557dep +122 → arr+95
10-09WN2876dep +42 → arr+64

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
PWMPortland +4 min smooth 🌤 clear · N 0 kt Full PWM delay board →
MDWChicago +30 min heavy ⛅ overcast · WNW 15 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at MDW: 40% odds of a 15+ minute delay and around +12 min expected when it bites, measured from this route's own weather-matched delay history. See live delays → · Weather risk by airport →

How the Portland to Chicago route actually runs

Pro Flight Search records official board updates for nonstop PWM to MDW 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 — Portland (PWM) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

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

PWM to MDW questions

Is PWM–MDW running on time right now?

Mostly on schedule. The arrival side at MDW is the weaker end, route health score 75/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on PWM–MDW?

Operators schedule morning departures around 06:30 and evening departures around 18:00 from PWM. Earlier flights typically land before destination-airport delays accumulate later in the day; check the MDW delay card to confirm conditions when you'd arrive.

How long is the flight from PWM to MDW?

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 PWM–MDW fly?

Southwest Airlines runs the route with about 7 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.