SJU (San Juan) to MDW (Chicago) flights arrive on time 60% of the time. The most reliable airline on this route is Frontier Airlines at 60%. The average delay is 48 minutes. Delays on this route are most often caused by the incoming plane arriving late.
Source: Bureau of Transportation Statistics. Updated March 2026.SJU → MDW
SJU (San Juan) to MDW (Chicago)
SJU → MDW on-time performance by month
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This route is frequently delayed. About 60% of flights arrive on schedule.
Delays on this route are most often caused by the incoming plane arriving late.
Accurate?
Airlines are roughly equal on this route — Frontier Airlines leads slightly at 60% vs Southwest Airlines at 60%.
Airline Comparison
Frontier Airlines leads at 60% on time; Southwest Airlines trails at 60%.
Accurate?
Good to know
Departing from SJU
75% on timeExpect ~17 min sitting on the taxiway after your gate pushes back. SJU has long runway queues.
TSA is currently ~7 min. Best time: 4 AM (about 7 min).
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 ~5 min right now. Allow at least 60 minutes for a domestic connection.
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Data last updated March 2026. Source: Bureau of Transportation Statistics.