San Diego (SAN) to Chicago (MDW): On-Time Performance
Data through May 2026
San Diego (SAN) to Chicago (MDW) effectively runs on two schedules. In October 2025, 88% of arrivals were on time; in July 2024 that fell to 62% — a 26-point seasonal swing. Across the full period the route averages 76% on-time against a national 78%. Morning departures also hold up better than evening ones (84% vs 69%), which matters most in the rough months.
- On-time
- 76%
- arrived <15 min late
- Avg delay
- 13 min
- completed flights
- Cancelled
- 0.7%
- Flights/day
- 2.9
- last 12 months
- Duration
- 3h 58m
- scheduled
- Distance
- 1,728 mi
Monthly on-time trend
Best time to fly from SAN to MDW
Aim for departures around 10 p.m. (98% on-time); avoid 7 p.m. departures (51%).
By day of week
| Day | On-time | Avg delay |
|---|---|---|
| Monday | 78% | 12 min |
| Tuesday | 77% | 10 min |
| Wednesday | 78% | 9 min |
| Thursday | 74% | 20 min |
| Friday | 72% | 16 min |
| Saturdaybest | 83% | 8 min |
| Sunday | 74% | 15 min |
What causes delays on this route
Share of total delay minutes by cause, as reported by carriers to the US DOT.
- Late-arriving aircraft54%
- Airline operations29%
- National airspace system16%
- Security1%
Frequently asked questions
- How often are flights from SAN to MDW delayed?
- 24% of SAN–MDW flights arrived 15 or more minutes late (the US DOT definition of a delay) between 2024-06 and 2026-05. The average arrival delay across completed flights was 13 minutes.
- What is the best time of day to fly from SAN to MDW?
- Departures around 10 p.m. have the best record (98% on-time), while departures around 7 p.m. have the worst (51%). As on most US routes, delays accumulate through the day, so earlier flights are generally safer.
- How long is the flight from SAN to MDW?
- The scheduled SAN–MDW flight time averages 3h 58m over 1,728 miles. Actual arrival times vary — flights on this route land 15+ minutes late 24% of the time.
- How often are SAN to MDW flights cancelled?
- 0.7% of scheduled flights on this route were cancelled between 2024-06 and 2026-05, at or below the national rate of 1.6%.
- What is the worst month to fly from SAN to MDW?
- July 2024 was the roughest month in this dataset, with only 62% of arrivals on time. The best was October 2025 at 88%. If your dates are flexible, that 26-point gap is worth planning around.
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Based on 2,090 flights, 2024-06–2026-05. Source: US DOT Bureau of Transportation Statistics. Updated 2026-07-01.