75% of flights from White Plains to Chicago arrived on time over the past 12 months. That is worse than the typical U.S. route. The 7 a.m. departures ran on time 88% of the time; the 5 p.m. ones 61%. 15% 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 HPN → ORD: when a flight was late, it was under 45 minutes late 39% of the time. About 1 in 10 flights landed an hour or more late, and 1 in 31 three hours or more; 4.1% were cancelled outright.
- On time or early75%
- 15–30 min late5.3%
- 30–60 min late5.3%
- 1–2 hours late5.1%
- 2–3 hours late2.0%
- 3+ hours late3.2%
- Diverted0.4%
- Cancelled4.1%
Share of all 1,561 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 |
|---|---|---|---|---|---|---|---|
| American Airlines | 1,561 | 75% | 4.1% | −10 min | 10.3% | +94 min | Envoy |
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 HPN). Delays build through the day as late planes knock on, so early flights usually do best.
Last flight of the day
On HPN → ORD, each airline's last flight of the day was cancelled 7.2% of the time, against 3.1% for its earlier flights (2.3× as often). It arrived 3+ hours late 4.7% of the time (earlier flights: 2.8%). 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 | 5:45 p.m. | 7.2% | 4.7% | 3.1% | first flight 6:19 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 ORD tonight, book an earlier flight so there's a backup if it's cancelled.
By month
Each calendar month pooled over 2023–2026. Best: September (82%). Worst: January (70%).
By day of week
| Day | Flights | On time | Cancelled |
|---|---|---|---|
| Monday | 233 | 69% | 8.2% |
| Tuesday | 218 | 77% | 2.8% |
| Wednesday | 211 | 75% | 1.4% |
| Thursday | 223 | 75% | 2.7% |
| Friday | 225 | 72% | 2.7% |
| Saturday | 224 | 83% | 5.8% |
| Sunday | 227 | 72% | 4.9% |
Why flights were late
Share of delay minutes on flights 15+ minutes late, as reported to BTS by the airlines.
Cancellations: weather 41 · air traffic/airport 20 · airline 3
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 |
|---|---|---|---|---|---|---|
| AA 3751 | 6:00 a.m. | 161 | 90% | 0.6% | −15 min | Envoy |
| AA 3496 | 7:10 a.m. | 361 | 85% | 2.8% | −14 min | Envoy |
| AA 3812 | 12:00 p.m. | 358 | 76% | 2.8% | −7 min | Envoy |
| AA 3808 | 4:30 p.m. | 353 | 66% | 4.3% | −4 min | Envoy |
Worst days in the past year
| Date | Flights | On time | Cancelled |
|---|---|---|---|
| Nov 10, 2025 | 5 | 0% | 2 |
| Dec 7, 2025 | 5 | 0% | 1 |
| Mar 13, 2026 | 4 | 0% | 0 |
| Dec 29, 2025 | 4 | 0% | 1 |
| Apr 2, 2026 | 4 | 0% | 2 |
Nearby airport alternatives
Other ways to make the same trip, using airports within 60 miles of White Plains or Chicago. None has been clearly more reliable than HPN → ORD.
| Route | Flights | On time | Cancelled |
|---|---|---|---|
| HPN → ORD (this route) | 1,561 | 75% | 4.1% |
| EWR → ORD Newark to Chicago O'Hare | 6,123 | 68% | 3.9% |
| JFK → ORD New York JFK to Chicago O'Hare | 3,245 | 67% | 6.5% |
| LGA → MDW LaGuardia to Chicago Midway | 2,391 | 66% | 5.2% |
| LGA → ORD LaGuardia to Chicago O'Hare | 11,641 | 63% | 5.4% |
Questions
How often are flights from HPN to ORD on time?
75% of 1,561 scheduled flights from White Plains, NY to Chicago, IL arrived within 15 minutes of schedule between September 2025 and August 2026. 4.1% were cancelled.
What is the best time of day to fly HPN to ORD?
Flights scheduled to leave at 7 a.m. were the most reliable (88% on time). The 5 p.m. departures were the least (61%).
What month has the most delays from HPN to ORD?
January (70% on time). The best month is September (82%), over 2023–2026.
Is the last flight of the day from HPN to ORD more likely to be cancelled?
Yes. Each airline's last HPN–ORD flight of the day was cancelled 7.2% of the time over the past year, against 3.1% for its earlier flights. If the last flight is cancelled, the next one is usually the following morning.
Related
- ORD → HPN (return)
- Westchester (HPN) delays by hour
- Flights into Chicago O'Hare (ORD)
- American 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.