Chicago (MDW) to Oakland (OAK): On-Time Performance
Data through July 2026
The calendar drives reliability on MDW–OAK. January 2025 flights landed on schedule 88% of the time, but December 2025 dropped to 36% — a gap of 51 points. Across the full period the route averages 70% on-time against a national 78%. Morning departures also hold up better than evening ones (77% vs 59%), which matters most in the rough months.
- On-time
- 70%
- arrived <15 min late
- Avg delay
- 17 min
- completed flights
- Cancelled
- 0.7%
- Flights/day
- 1.4
- last 12 months
- Duration
- 4h 36m
- scheduled
- Distance
- 1,844 mi
Monthly on-time trend
Best time to fly from MDW to OAK
Aim for departures around 6 a.m. (87% on-time); avoid 9 p.m. departures (51%).
By day of week
| Day | On-time | Avg delay |
|---|---|---|
| Monday | 62% | 24 min |
| Tuesdaybest | 78% | 15 min |
| Wednesday | 68% | 15 min |
| Thursday | 68% | 16 min |
| Friday | 72% | 17 min |
| Saturday | 75% | 13 min |
| Sunday | 64% | 19 min |
What causes delays on this route
Share of total delay minutes by cause, as reported by carriers to the US DOT.
- Late-arriving aircraft40%
- Airline operations36%
- National airspace system17%
- Weather7%
Frequently asked questions
- How often are flights from MDW to OAK delayed?
- 31% of MDW–OAK 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 17 minutes.
- What is the best time of day to fly from MDW to OAK?
- Departures around 6 a.m. have the best record (87% on-time), while departures around 9 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 MDW to OAK?
- The scheduled MDW–OAK flight time averages 4h 36m over 1,844 miles. Actual arrival times vary — flights on this route land 15+ minutes late 31% of the time.
- How often are MDW to OAK flights cancelled?
- 0.7% 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 MDW to OAK?
- December 2025 was the roughest month in this dataset, with only 36% of arrivals on time. The best was January 2025 at 88%. If your dates are flexible, that 51-point gap is worth planning around.
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Based on 1,073 flights, 2024-07–2026-07. Source: US DOT Bureau of Transportation Statistics. Updated 2026-09-28.