Best Time to Fly MDW to OAK: On-Time Stats by Hour & Airline
Chicago Midway International → Oakland International
Data through July 2026 · Last updated October 18, 2026
505 flights were scheduled from Chicago (MDW) to Oakland (OAK) in the last 12 months, and 64.1% of those that flew arrived on time, 13.6 points below the US average of 77.6%.
Southwest Airlines was the only reporting airline with regular flights on this route.
Over 24 months, Tuesday was the most reliable day (78% on time) and December the worst month (52%).
The cancellation rate was 1.4% (US average 1.8%).
MDW to OAK on-time performance by airline
Last 12 months. Airlines with fewer than 30 completed flights are marked “limited data”.
| Airline | On time | Avg delay when late | Cancelled | Flights |
|---|---|---|---|---|
| Southwest Airlines | 64.1% | 53 min | 1.4% | 505 |
80%+ good 70–79.9% fair <70% poor
Best time of day to fly MDW to OAK
On-time arrival % by scheduled departure hour (local time), 984 flights over 24 months.
Show the numbers
| Departure hour | On time | Cancelled | Flights |
|---|---|---|---|
| 5am–6am | Limited data | 3 | |
| 6am–7am | Limited data | 27 | |
| 7am–8am | 58.4% | 1.3% | 78 |
| 8am–9am | 84.3% | 0.0% | 103 |
| 9am–10am | 85.7% | 0.0% | 56 |
| 10am–11am | 74.8% | 1.6% | 121 |
| 11am–12pm | 75.6% | 0.0% | 41 |
| 12pm–1pm | Limited data | 8 | |
| 1pm–2pm | 69.8% | 0.0% | 53 |
| 2pm–3pm | Limited data | 4 | |
| 3pm–4pm | 81.0% | 0.0% | 42 |
| 4pm–5pm | 64.3% | 0.0% | 98 |
| 5pm–6pm | 71.4% | 0.0% | 77 |
| 6pm–7pm | Limited data | 14 | |
| 7pm–8pm | 70.2% | 0.0% | 57 |
| 8pm–9pm | 62.5% | 0.0% | 48 |
| 9pm–10pm | 50.7% | 2.0% | 147 |
| 10pm–11pm | Limited data | 7 | |
Best day of the week
24 months, by day of departure.
Best month to fly
24 months, by calendar month.
Holiday travel on MDW to OAK
On-time arrivals during holiday periods compared with all other days, last 24 months.
| Period | On time | vs other days | Cancelled | Flights |
|---|---|---|---|---|
| Thanksgiving week (Tue before to Mon after) | Limited data | 18 | ||
| Christmas & New Year (Dec 20 - Jan 3) | 40.0% | -32.3 pts | 0.0% | 35 |
| Summer peak (Jun 15 - Aug 15) | 63.9% | -8.4 pts | 0.5% | 193 |
| All other days | 72.3% | — | 0.7% | 738 |
Monthly on-time trend
On-time arrival % each month, with the 12-month US average for reference.
What causes delays on this route
Share of reported delay minutes, last 12 months (BTS cause categories).