MDW (Chicago) to PWM (Portland) flights arrive on time 86% of the time. The most reliable airline on this route is Southwest Airlines at 86%. The average delay is 49 minutes. Delays on this route are most often caused by the airline (crew, maintenance, or boarding).
Source: Bureau of Transportation Statistics. Updated May 2026.MDW → PWM
MDW (Chicago) to PWM (Portland)
MDW → PWM on-time performance by month
24
25
JanFebMarAprMayJunJulAugSepOctNovDec
Worse
Better
This route is usually on time. About 86% of flights arrive on schedule.
Delays on this route are most often caused by the airline (crew, maintenance, or boarding).
Accurate?
Accurate?
Good to know
Departing from MDW
78% on timeTSA is currently ~25 min. Best time: 4 AM (about 5 min).
Arriving at PWM
81% on timeWhen flights into PWM are late, the average delay is 76 minutes. Build buffer if you have ground plans.
If connecting at PWM: TSA is ~11 min right now. Allow at least 60 minutes for a domestic connection.
PWM has a 2.8% cancellation rate — keep the airline app handy for rebooking.
Flight cancelled or delayed?
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Data last updated May 2026. Source: Bureau of Transportation Statistics.