Oakland (OAK) to Chicago (MDW): On-Time Performance
Data through May 2026
The calendar drives reliability on OAK–MDW. May 2025 flights landed on schedule 100% of the time, but July 2024 dropped to 65% — a gap of 35 points. Across the full period the route averages 84% on-time against a national 78%. Morning departures also hold up better than evening ones (90% vs 70%), which matters most in the rough months.
- On-time
- 84%
- arrived <15 min late
- Avg delay
- 8 min
- completed flights
- Cancelled
- 0.2%
- Flights/day
- 1.3
- last 12 months
- Duration
- 4h 5m
- scheduled
- Distance
- 1,844 mi
Monthly on-time trend
Best time to fly from OAK to MDW
Aim for departures around 6 a.m. (95% on-time); avoid 6 p.m. departures (53%).
By day of week
| Day | On-time | Avg delay |
|---|---|---|
| Monday | 80% | 8 min |
| Tuesdaybest | 88% | 5 min |
| Wednesday | 84% | 10 min |
| Thursday | 82% | 10 min |
| Friday | 82% | 8 min |
| Saturday | 85% | 6 min |
| Sunday | 86% | 8 min |
What causes delays on this route
Share of total delay minutes by cause, as reported by carriers to the US DOT.
- Late-arriving aircraft35%
- Airline operations49%
- National airspace system16%
Frequently asked questions
- How often are flights from OAK to MDW delayed?
- 16% of OAK–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 8 minutes.
- What is the best time of day to fly from OAK to MDW?
- Departures around 6 a.m. have the best record (95% on-time), while departures around 6 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 OAK to MDW?
- The scheduled OAK–MDW flight time averages 4h 5m over 1,844 miles. Actual arrival times vary — flights on this route land 15+ minutes late 16% of the time.
- How often are OAK to MDW flights cancelled?
- 0.2% 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 OAK to MDW?
- July 2024 was the roughest month in this dataset, with only 65% of arrivals on time. The best was May 2025 at 100%. If your dates are flexible, that 35-point gap is worth planning around.
Explore related pages
More routes from OAK
Other ways to fly to Chicago (MDW)
Related guides
Based on 1,036 flights, 2024-06–2026-05. Source: US DOT Bureau of Transportation Statistics. Updated 2026-07-01.