Southwest Airlines is the most reliable airline on the OAK to MDW route with a 85% on-time rate. Based on 2,116 flights tracked.
Source: Bureau of Transportation Statistics. Updated October 2026.Best Airline: OAK to MDW
Oakland to Chicago — airline reliability comparison
On-Time Rate by Airline
Southwest Airlines85%
OAK to MDW Airline Comparison
| Airline | On-Time % | Cancel % | Avg Delay | Flights |
|---|---|---|---|---|
| Southwest AirlinesWNBest | 85% | 0.4% | 41m | 2,116 |
Route Overview
83%
Overall On-Time
43m
Avg Delay
0.4%
Cancel Rate
2,116
Total Flights
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Data last updated October 2026. Source: Bureau of Transportation Statistics.