SJU (San Juan) to MDW (Chicago) flights arrive on time 72% of the time. The most reliable airline on this route is Frontier Airlines at 73%. The average delay is 53 minutes. Delays on this route are most often caused by the incoming plane arriving late.
Source: Bureau of Transportation Statistics. Updated October 2026.SJU → MDW
SJU (San Juan) to MDW (Chicago)
SJU → MDW on-time performance by month
23
24
JanFebMarAprMayJunJulAugSepOctNovDec
Worse
Better
This route is delayed fairly often. About 72% of flights arrive on schedule.
Delays on this route are most often caused by the incoming plane arriving late.
Accurate?
Frontier Airlines edges out Southwest Airlines on this route — 73% vs 60% on time.
Airline Comparison
Frontier Airlines leads at 73% on time; Southwest Airlines trails at 60%.
Accurate?
Good to know
Departing from SJU
75% on timeExpect ~18 min sitting on the taxiway after your gate pushes back. SJU has long runway queues.
TSA is currently ~15 min. Best time: 4 AM (about 7 min).
Arriving at MDW
79% on timeWhen flights into MDW are late, the average delay is 57 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?
Check what Frontier Airlines owes you — refund rights, action plan, complaint email. Free.
Flying out of SJU? We'll brief you.
Delays, TSA, weather, gates — we'll let you know if something matters.
Know someone flying soon?
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Data last updated October 2026. Source: Bureau of Transportation Statistics.