Best Time to Fly BOS to MDW: On-Time Stats by Hour & Airline
Logan International → Chicago Midway International
Data through July 2026 · Last updated October 18, 2026
1,361 flights were scheduled from Boston (BOS) to Chicago (MDW) in the last 12 months, and 72.2% of those that flew arrived on time, 5.4 points below the US average of 77.6%.
Southwest Airlines was the only reporting airline with regular flights on this route.
January has been the best month (85% on time) and Sunday the weakest day of the week (71%).
1.9% of flights were cancelled, versus 1.8% nationally.
BOS 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 | 72.2% | 63 min | 1.9% | 1,361 |
80%+ good 70–79.9% fair <70% poor
Best time of day to fly BOS to MDW
On-time arrival % by scheduled departure hour (local time), 2,685 flights over 24 months.
Show the numbers
| Departure hour | On time | Cancelled | Flights |
|---|---|---|---|
| 5am–6am | 92.8% | 1.6% | 382 |
| 6am–7am | 94.3% | 2.1% | 143 |
| 7am–8am | 92.6% | 0.8% | 248 |
| 8am–9am | 84.7% | 1.6% | 126 |
| 9am–10am | 93.2% | 0.0% | 117 |
| 10am–11am | 95.9% | 0.0% | 122 |
| 11am–12pm | 92.3% | 0.0% | 78 |
| 12pm–1pm | 87.9% | 0.0% | 99 |
| 1pm–2pm | 76.2% | 0.5% | 194 |
| 2pm–3pm | 77.8% | 0.6% | 177 |
| 3pm–4pm | 59.6% | 1.4% | 143 |
| 4pm–5pm | 61.2% | 0.0% | 103 |
| 5pm–6pm | 54.3% | 2.4% | 250 |
| 6pm–7pm | 50.2% | 2.6% | 270 |
| 7pm–8pm | 57.0% | 2.5% | 81 |
| 8pm–9pm | 40.4% | 2.0% | 102 |
| 9pm–10pm | 61.0% | 2.4% | 42 |
| 10pm–11pm | Limited data | 8 | |
Best day of the week
24 months, by day of departure.
Best month to fly
24 months, by calendar month.
Holiday travel on BOS 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) | 81.6% | +3.5 pts | 5.7% | 53 |
| Christmas & New Year (Dec 20 - Jan 3) | 69.3% | -8.8 pts | 1.9% | 103 |
| Summer peak (Jun 15 - Aug 15) | 69.0% | -9.1 pts | 1.6% | 628 |
| All other days | 78.1% | — | 1.1% | 1,901 |
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).