SJU to MDW flight delays
San Juan, PR (SJU) Chicago, IL (MDW) · 2,057 miles
53 flights · January 2025 – August 2026 · US Bureau of Transportation Statistics
67.31%
Arrived on time
Within 15 minutes of schedule
1.89%
Cancelled
Share of scheduled flights
47 min
When late, late by
Average across delayed arrivals
17 min
Delay per flight
Averaged over every flight flown
What the record says about this route
This route does worse than its own airport. SJU as a whole runs 9.3 points more punctual than these flights, which points at something specific to the route — the time of day it is scheduled, or the aircraft that feed it — rather than the airport.
This is a late route. Flights from San Juan to Chicago miss their scheduled arrival often enough that a tight connection at the far end is a connection at risk.
Every airline on SJU to MDW
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 | 67.31% | 1.89% | 47 min | — |
Month by month
Share of flights that arrived within 15 minutes of schedule, by month flown.
The return leg
MDW to SJU Chicago back to San Juan 69.23% on time —Other routes from San Juan
Common questions
Are flights from San Juan to Chicago usually delayed?
67.31% of flights on the SJU to MDW 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 SJU to MDW flights cancelled?
1.89% of scheduled flights did not operate — about 19 in every thousand. That is in the normal range.
When SJU to MDW flights are late, how late are they?
About 47 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 SJU to MDW 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 →