MDW to SJU flight delays
Chicago, IL (MDW) San Juan, PR (SJU) · 2,057 miles
53 flights · January 2025 – August 2026 · US Bureau of Transportation Statistics
69.23%
Arrived on time
Within 15 minutes of schedule
1.89%
Cancelled
Share of scheduled flights
46 min
When late, late by
Average across delayed arrivals
16 min
Delay per flight
Averaged over every flight flown
What the record says about this route
Flights from Chicago to San Juan run late more often than the average route, though not severely.
Every airline on MDW to SJU
Ranked by how many flights each one operated. A carrier with fewer than 100 flights in the period is listed but not graded.
| Airline | Flights | On time | Cancelled | Avg delay | Grade |
|---|---|---|---|---|---|
| Southwest Airlines | 53 | 69.23% | 1.89% | 46 min | — |
Month by month
Share of flights that arrived within 15 minutes of schedule, by month flown.
The return leg
SJU to MDW San Juan back to Chicago 67.31% on time —Other routes from Chicago
Common questions
Are flights from Chicago to San Juan usually delayed?
69.23% of flights on the MDW to SJU route arrived within 15 minutes of schedule, so roughly 3 in every ten arrived late. That is worse than the average route in this record.
How often are MDW to SJU flights cancelled?
1.89% of scheduled flights did not operate — about 19 in every thousand. That is in the normal range.
When MDW to SJU flights are late, how late are they?
About 46 minutes on average across the flights that arrived more than 15 minutes behind schedule.
What these figures do and do not tell you
Everything on this page is counted from the flights that actually operated on MDW to SJU during January 2025 – August 2026, as reported by the airlines to the US Bureau of Transportation Statistics. "On time" is the federal definition: arriving at the gate within 15 minutes of the scheduled time.
A route's record is a description of the past, not a forecast. Weather, air traffic control and the aircraft's earlier flights that day drive most delays, and none of them are predictable from a historical rate. What the record does tell you is whether this route runs late more often than others, and which carrier on it has the better history — which is the part you can actually act on when you book.
Cancellations are counted separately from delays because they are a different problem for a traveller: a late flight still gets you there. How the grade is calculated →