Southwest Airlines is the most reliable airline on the MDW to SJU route with a 90% on-time rate, compared to Frontier Airlines at 72%. Based on 10 flights tracked.
Source: Bureau of Transportation Statistics. Updated October 2026.Best Airline: MDW to SJU
Chicago to San Juan — airline reliability comparison
On-Time Rate by Airline
Southwest Airlines90%
Frontier Airlines72%
MDW to SJU Airline Comparison
| Airline | On-Time % | Cancel % | Avg Delay | Flights |
|---|---|---|---|---|
| Southwest AirlinesWNBest | 90% | 0.0% | 16m | 10 |
| Frontier AirlinesF9Worst | 72% | 3.1% | 64m | 234 |
Route Overview
69%
Overall On-Time
61m
Avg Delay
2.9%
Cancel Rate
278
Total Flights
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Data last updated October 2026. Source: Bureau of Transportation Statistics.