71% of flights from Chicago to San Juan arrived on time over the past 12 months. That is worse than the typical U.S. route. The 2 p.m. departures ran on time 79% of the time; the noon ones 57%. Most reliable airline: United Airlines (79%). 11% of flights arrived more than an hour late or not at all.
How late?
The on-time rate treats a flight 20 minutes late the same as one 5 hours late. Here's the split for ORD → SJU: when a flight was late, it was under 45 minutes late 55% of the time. About 1 in 11 flights landed an hour or more late, and 1 in 70 three hours or more; 2.2% were cancelled outright.
- On time or early71%
- 15–30 min late8.7%
- 30–60 min late8.4%
- 1–2 hours late5.8%
- 2–3 hours late1.7%
- 3+ hours late1.4%
- Diverted0.2%
- Cancelled2.2%
Share of all 1,390 scheduled flights, past 12 months, by arrival time against schedule.
By airline
| Airline | Flights | On time | Cancelled | Typical arrival | 1h+ late | Avg when late | Operated by |
|---|---|---|---|---|---|---|---|
| United Airlines | 657 | 79% | 0.3% | −4 min | 4.9% | +52 min | United Airlines |
| American Airlines | 429 | 70% | 1.6% | −2 min | 11.9% | +64 min | American Airlines |
| Spirit Airlines | 232 | 56% | 8.2% | +4 min | 12.9% | +76 min | Spirit Airlines |
| Frontier Airlines | 72 | — | — | — | — | — | Frontier Airlines |
Airline = the name on the ticket. Regional flights (e.g. "Delta Connection") count under the ticketing airline, and the operator is listed.
Best time of day to fly
On-time rate by scheduled departure hour (local time at ORD). Delays build through the day as late planes knock on, so early flights usually do best.
By airline and hour
| Departs | United Airlines | American Airlines | Spirit Airlines |
|---|---|---|---|
| 8 a.m. | 79% | 74% | — |
| noon | — | — | 57% |
| 2 p.m. | 79% | — | — |
Last flight of the day
On ORD → SJU, each airline's last flight of the day was cancelled 3.3% of the time, against 1.4% for its earlier flights (2.4× as often). It arrived 3+ hours late 0.9% of the time (earlier flights: 0.9%). It matters more than the numbers suggest. Miss an earlier flight and there's another one that evening; miss the last one and you're usually waiting until morning.
| Airline | Last departure | Last: cancelled | Last: 3h+ late | Earlier: cancelled | Next morning |
|---|---|---|---|---|---|
| American Airlines | 5:50 p.m. | 2.8% | 0.0% | 2.8% | first flight 5:50 p.m. |
| United Airlines | 2:38 p.m. | 0.4% | 0.4% | 0.3% | first flight 8:49 a.m. |
Last flight = the airline's last scheduled departure on this route that day, on days it flies the route at least twice; past 12 months. Times are typical scheduled times over the latest three months.
If you need to be in SJU tonight, book an earlier flight so there's a backup if it's cancelled.
By month
Each calendar month pooled over 2023–2026. Best: February (89%). Worst: August (67%).
By day of week
| Day | Flights | On time | Cancelled |
|---|---|---|---|
| Monday | 210 | 65% | 3.3% |
| Tuesday | 188 | 73% | 2.1% |
| Wednesday | 185 | 78% | 0.0% |
| Thursday | 199 | 74% | 1.5% |
| Friday | 206 | 72% | 1.5% |
| Saturday | 202 | 68% | 5.0% |
| Sunday | 200 | 70% | 2.0% |
Why flights were late
Share of delay minutes on flights 15+ minutes late, as reported to BTS by the airlines.
Cancellations: weather 16 · airline 8 · air traffic/airport 7
Month by month
Flight numbers on this route
Regular flights with at least 120 scheduled trips in the past year. Sorted by departure time.
| Flight | Departs | Flights | On time | Cancelled | Typical arrival | Operated by |
|---|---|---|---|---|---|---|
| UA 1996 | 8:55 a.m. | 365 | 79% | 0.3% | −5 min | United Airlines |
| UA 695 | 2:20 p.m. | 288 | 79% | 0.4% | −4 min | United Airlines |
Worst days in the past year
| Date | Flights | On time | Cancelled |
|---|---|---|---|
| Mar 26, 2026 | 6 | 0% | 1 |
| Mar 16, 2026 | 6 | 0% | 1 |
| Mar 15, 2026 | 6 | 0% | 1 |
| Jan 3, 2026 | 5 | 0% | 5 |
| Jan 30, 2026 | 5 | 0% | 1 |
Questions
How often are flights from ORD to SJU on time?
71% of 1,390 scheduled flights from Chicago, IL to San Juan, PR arrived within 15 minutes of schedule between September 2025 and August 2026. 2.2% were cancelled.
What is the best time of day to fly ORD to SJU?
Flights scheduled to leave at 2 p.m. were the most reliable (79% on time). The noon departures were the least (57%).
Which airline is most on time from ORD to SJU?
United Airlines: 79% of its 657 flights on the route arrived on time. American Airlines: 70%. Spirit Airlines: 56%.
What month has the most delays from ORD to SJU?
August (67% on time). The best month is February (89%), over 2023–2026.
Is the last flight of the day from ORD to SJU more likely to be cancelled?
Yes. Each airline's last ORD–SJU flight of the day was cancelled 3.3% of the time over the past year, against 1.4% for its earlier flights. If the last flight is cancelled, the next one is usually the following morning.
Related
- SJU → ORD (return)
- Chicago O'Hare (ORD) delays by hour
- Flights into San Juan (SJU)
- United Airlines on-time record
- American Airlines on-time record
- Spirit Airlines on-time record
- Frontier Airlines on-time record
- Connecting off this flight? Check the risk
Domestic flights by the airlines that report to the U.S. DOT, plus their regional partners. "On time" means arriving less than 15 minutes after schedule; cancelled and diverted flights count as not on time. Past performance is a guide, not a forecast. Method.