Southwest Airlines is the most reliable airline on the PDX to MDW route with a 90% on-time rate. Based on 2,097 flights tracked.
Source: Bureau of Transportation Statistics. Updated October 2026.Best Airline: PDX to MDW
Portland to Chicago — airline reliability comparison
On-Time Rate by Airline
Southwest Airlines90%
PDX to MDW Airline Comparison
| Airline | On-Time % | Cancel % | Avg Delay | Flights |
|---|---|---|---|---|
| Southwest AirlinesWNBest | 90% | 0.6% | 38m | 2,097 |
Route Overview
89%
Overall On-Time
39m
Avg Delay
0.5%
Cancel Rate
2,097
Total Flights
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Data last updated October 2026. Source: Bureau of Transportation Statistics.