Best Time to Fly OAK to MDW: On-Time Stats by Hour & Airline
Oakland International → Chicago Midway International
Data through July 2026 · Last updated October 18, 2026
Over the last 12 months, 84.6% of Oakland (OAK) to Chicago (MDW) flights arrived on time (505 scheduled flights). That is 7.0 points above the national average of 77.6%.
Southwest Airlines was the only reporting airline with regular flights on this route.
February has been the best month (93% on time) and Monday the weakest day of the week (82%).
0.2% of flights were cancelled, versus 1.8% nationally.
OAK to MDW 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 | 84.6% | 34 min | 0.2% | 505 |
80%+ good 70–79.9% fair <70% poor
Best time of day to fly OAK to MDW
On-time arrival % by scheduled departure hour (local time), 980 flights over 24 months.
Show the numbers
| Departure hour | On time | Cancelled | Flights |
|---|---|---|---|
| 5am–6am | 91.4% | 0.3% | 365 |
| 6am–7am | 95.8% | 0.0% | 120 |
| 7am–8am | Limited data | 11 | |
| 8am–9am | Limited data | 16 | |
| 9am–10am | Limited data | 13 | |
| 10am–11am | 83.3% | 0.0% | 43 |
| 11am–12pm | 86.0% | 0.8% | 123 |
| 12pm–1pm | Limited data | 25 | |
| 1pm–2pm | 79.4% | 0.0% | 35 |
| 2pm–3pm | Limited data | 7 | |
| 3pm–4pm | Limited data | 9 | |
| 5pm–6pm | Limited data | 12 | |
| 6pm–7pm | 59.6% | 0.0% | 52 |
| 11pm–12am | 78.5% | 0.0% | 149 |
Best day of the week
24 months, by day of departure.
Best month to fly
24 months, by calendar month.
Holiday travel on OAK to MDW
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) | 91.4% | +4.2 pts | 0.0% | 35 |
| Summer peak (Jun 15 - Aug 15) | 82.0% | -5.3 pts | 0.0% | 191 |
| All other days | 87.3% | — | 0.3% | 736 |
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).