PDX → MDWPortland to Chicago

live

Direct flights from Portland (PDX) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 86% of the last 14 operated flights arrived within 15 minutes of schedule. The median arrival is 4 minutes early. No cancellations were recorded across the 14 tracked flights. The nonstop covers 2,811 km, an estimated 4 hours 6 minutes in the air. Measured by Pro Flight Search from live flight boards at Portland and Chicago. Updated 24 October 2026 at 20:22 UTC.

Today, PDX → MDW

Sat 24 Oct · local times
  1. 23:35 WN2737Southwest On scheduleGate E12 ·

Checked PDX board 13:22 · MDW board 14:22

PDX Portland smooth · +6
MDW Chicago smooth · +0
2,811 km · ~4h 06m est.
dep bank 05:20–23:357x weekly
Runs reliable · 1 airline · 7x weekly · nonstop
86% on time

of the last 14 operated PDX → MDW flights arrived within 15 minutes

Median arrival delay is −4 min. 0 of 14 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−4 minacross the last 14 operated legs
Flight time~4h 06mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 14

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 AirlinesWN86% on time

Flights WN3319 05:20 Su · WN799 05:20 Mo Th Fr · WN1567 06:15 Tu We · WN2737 23:35 Sa

History

operated legs · board outcomes
10-23WN3320dep +47 → arr+33
10-23WN799dep −3 → arr−5
10-22WN3320dep +4 → arr−3
10-22WN799dep +0 → arr−13
10-21WN1567dep −2 → arr−9
10-21WN3320arrived−4
10-20WN1567dep +4 → arr+13
10-20WN3320arrived−24
10-19WN3320arrived−15
10-19WN799dep +0 → arr−6
10-18WN3319dep +0 → arr−2
10-18WN3320dep +84 → arr+93
10-17WN2737arrived+7
10-16WN3320arrived−17

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
PDXPortland +6 min smooth 🌤 overcast · WNW 4 kt Full PDX delay board →
MDWChicago +0 min smooth 🌤 scattered clouds · SSE 8 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at PDX and MDW: 40% odds of a 15+ minute delay and around +9 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 PDX 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 (PDX) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

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

PDX to MDW questions

Is PDX–MDW running on time right now?

Smooth skies ahead. The departure side at PDX is the weaker end, route health score 95/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on PDX–MDW?

Operators schedule morning departures around 05:20 and evening departures around 23:35 from PDX. 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 PDX to MDW?

Great-circle distance is 2,811 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 228–271 min gate-to-gate on this route.

How often does PDX–MDW fly?

Southwest Airlines runs the route with about 13 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.