Best Time to Fly MDW to BOS: On-Time Stats by Hour & Airline
Chicago Midway International → Logan International
Data through July 2026 · Last updated October 18, 2026
Over the last 12 months, 66.8% of Chicago (MDW) to Boston (BOS) flights arrived on time (1,360 scheduled flights). That is 10.8 points below the national average of 77.6%.
Southwest Airlines was the only reporting airline with regular flights on this route.
Over 24 months, Saturday was the most reliable day (80% on time) and June the worst month (62%).
The cancellation rate was 1.2% (US average 1.8%).
MDW to BOS 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 | 66.8% | 63 min | 1.2% | 1,360 |
80%+ good 70–79.9% fair <70% poor
Best time of day to fly MDW to BOS
On-time arrival % by scheduled departure hour (local time), 2,703 flights over 24 months.
Show the numbers
| Departure hour | On time | Cancelled | Flights |
|---|---|---|---|
| 5am–6am | 95.7% | 0.0% | 115 |
| 6am–7am | 94.1% | 0.0% | 169 |
| 7am–8am | 89.4% | 0.0% | 198 |
| 8am–9am | 85.0% | 0.0% | 193 |
| 9am–10am | 86.4% | 2.0% | 247 |
| 10am–11am | 86.5% | 0.0% | 141 |
| 11am–12pm | Limited data | 27 | |
| 12pm–1pm | 63.6% | 0.0% | 187 |
| 1pm–2pm | 58.5% | 0.5% | 214 |
| 2pm–3pm | 59.4% | 0.0% | 161 |
| 3pm–4pm | 50.7% | 1.4% | 138 |
| 4pm–5pm | 41.0% | 1.0% | 101 |
| 5pm–6pm | 70.5% | 0.0% | 132 |
| 6pm–7pm | 63.1% | 1.2% | 319 |
| 7pm–8pm | 55.2% | 3.2% | 187 |
| 8pm–9pm | 63.1% | 2.1% | 144 |
| 9pm–10pm | Limited data | 21 | |
| 10pm–11pm | Limited data | 9 | |
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 BOS
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) | 72.0% | -1.2 pts | 5.7% | 53 |
| Christmas & New Year (Dec 20 - Jan 3) | 71.6% | -1.6 pts | 1.0% | 103 |
| Summer peak (Jun 15 - Aug 15) | 64.5% | -8.7 pts | 1.4% | 627 |
| All other days | 73.2% | — | 0.5% | 1,920 |
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).