PWM (Portland) to MDW (Chicago) flights arrive on time 76% of the time. The most reliable airline on this route is Southwest Airlines at 76%. The average delay is 104 minutes. Delays on this route are most often caused by the incoming plane arriving late.
Source: Bureau of Transportation Statistics. Updated March 2026.PWM → MDW
PWM (Portland) to MDW (Chicago)
PWM → MDW on-time performance by month
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This route is on time most of the time. About 76% of flights arrive on schedule.
Delays on this route are most often caused by the incoming plane arriving late.
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Good to know
Departing from PWM
81% on timeExpect ~18 min sitting on the taxiway after your gate pushes back. PWM has long runway queues.
TSA is currently ~21 min. Best time: 4 AM (about 5 min).
PWM cancels 2.8% of flights — higher than average. Have a backup plan.
Arriving at MDW
78% on timeWhen flights into MDW are late, the average delay is 56 minutes. Build buffer if you have ground plans.
If connecting at MDW: TSA is ~16 min right now. Allow at least 60 minutes for a domestic connection.
Flight cancelled or delayed?
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Data last updated March 2026. Source: Bureau of Transportation Statistics.