San Diego (SAN) to Chicago (MDW): On-Time Performance
Data through July 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 77% on-time against a national 78%. Morning departures also hold up better than evening ones (84% vs 72%), which matters most in the rough months.
- On-time
- 77%
- arrived <15 min late
- Avg delay
- 13 min
- completed flights
- Cancelled
- 0.8%
- Flights/day
- 3.0
- 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. (95% on-time); avoid 3 p.m. departures (53%).
By day of week
| Day | On-time | Avg delay |
|---|---|---|
| Monday | 76% | 12 min |
| Tuesday | 78% | 9 min |
| Wednesday | 80% | 9 min |
| Thursday | 73% | 21 min |
| Friday | 75% | 15 min |
| Saturdaybest | 85% | 7 min |
| Sunday | 73% | 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 aircraft52%
- Airline operations30%
- National airspace system16%
- Security1%
Frequently asked questions
- How often are flights from SAN to MDW delayed?
- 23% of SAN–MDW flights arrived 15 or more minutes late (the US DOT definition of a delay) between 2024-07 and 2026-07. 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 (95% on-time), while departures around 3 p.m. have the worst (53%). 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 23% of the time.
- How often are SAN to MDW flights cancelled?
- 0.8% of scheduled flights on this route were cancelled between 2024-07 and 2026-07, 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 2,199 flights, 2024-07–2026-07. Source: US DOT Bureau of Transportation Statistics. Updated 2026-09-28.