68% of flights from Boston to Chicago arrived on time over the past 12 months. That is worse than the typical U.S. route. The 7 a.m. departures ran on time 89% of the time; the 6 p.m. ones 41%. 13% of flights arrived more than an hour late or not at all.
How late?
The on-time rate treats a flight 20 minutes late the same as one 5 hours late. Here's the split for BOS → MDW: when a flight was late, it was under 45 minutes late 51% of the time. About 1 in 10 flights landed an hour or more late, and 1 in 72 three hours or more; 2.0% were cancelled outright.
- On time or early68%
- 15–30 min late10%
- 30–60 min late9.4%
- 1–2 hours late6.7%
- 2–3 hours late2.1%
- 3+ hours late1.4%
- Diverted0.7%
- Cancelled2.0%
Share of all 1,368 scheduled flights, past 12 months, by arrival time against schedule.
By airline
| Airline | Flights | On time | Cancelled | Typical arrival | 1h+ late | Avg when late | Operated by |
|---|---|---|---|---|---|---|---|
| Southwest Airlines | 1,368 | 68% | 2.0% | −1 min | 10.2% | +63 min | Southwest Airlines |
Airline = the name on the ticket. Regional flights (e.g. "Delta Connection") count under the ticketing airline, and the operator is listed.
Best time of day to fly
On-time rate by scheduled departure hour (local time at BOS). Delays build through the day as late planes knock on, so early flights usually do best.
Last flight of the day
On BOS → MDW, each airline's last flight of the day was cancelled 4.1% of the time, against 1.2% for its earlier flights (3.4× as often). It arrived 3+ hours late 1.6% of the time (earlier flights: 1.4%). It matters more than the numbers suggest. Miss an earlier flight and there's another one that evening; miss the last one and you're usually waiting until morning.
| Airline | Last departure | Last: cancelled | Last: 3h+ late | Earlier: cancelled | Next morning |
|---|---|---|---|---|---|
| Southwest Airlines | 6:45 p.m. | 4.1% | 1.6% | 1.2% | first flight 5:35 a.m. |
Last flight = the airline's last scheduled departure on this route that day, on days it flies the route at least twice; past 12 months. Times are typical scheduled times over the latest three months.
If you need to be in MDW tonight, book an earlier flight so there's a backup if it's cancelled.
By month
Each calendar month pooled over 2023–2026. Best: November (86%). Worst: July (67%).
By day of week
| Day | Flights | On time | Cancelled |
|---|---|---|---|
| Monday | 208 | 60% | 3.4% |
| Tuesday | 181 | 70% | 2.2% |
| Wednesday | 177 | 74% | 1.1% |
| Thursday | 201 | 68% | 2.0% |
| Friday | 208 | 71% | 1.4% |
| Saturday | 184 | 72% | 2.2% |
| Sunday | 209 | 61% | 1.4% |
Why flights were late
Share of delay minutes on flights 15+ minutes late, as reported to BTS by the airlines.
Cancellations: weather 19 · air traffic/airport 5 · airline 3
Month by month
Worst days in the past year
| Date | Flights | On time | Cancelled |
|---|---|---|---|
| Aug 2, 2026 | 5 | 0% | 0 |
| Dec 28, 2025 | 4 | 0% | 0 |
| Jul 4, 2026 | 4 | 0% | 1 |
| Jul 18, 2026 | 4 | 0% | 0 |
| Nov 10, 2025 | 3 | 0% | 1 |
Nearby airport alternatives
Other ways to make the same trip, using airports within 60 miles of Boston or Chicago. MHT → MDW has been 15 points more reliable.
| Route | Flights | On time | Cancelled |
|---|---|---|---|
| BOS → MDW (this route) | 1,368 | 68% | 2.0% |
| MHT → MDW Manchester-Boston to Chicago Midway | 529 | 83% | 0.8% |
| PVD → MDW Rhode Island T. F. Green to Chicago Midway | 778 | 81% | 1.4% |
| MHT → ORD Manchester-Boston to Chicago O'Hare | 614 | 81% | 2.1% |
| PVD → ORD Rhode Island T. F. Green to Chicago O'Hare | 1,727 | 71% | 4.0% |
| BOS → ORD Boston Logan to Chicago O'Hare | 7,860 | 69% | 3.0% |
Questions
How often are flights from BOS to MDW on time?
68% of 1,368 scheduled flights from Boston, MA to Chicago, IL arrived within 15 minutes of schedule between September 2025 and August 2026. 2.0% were cancelled.
What is the best time of day to fly BOS to MDW?
Flights scheduled to leave at 7 a.m. were the most reliable (89% on time). The 6 p.m. departures were the least (41%).
What month has the most delays from BOS to MDW?
July (67% on time). The best month is November (86%), over 2023–2026.
Is the last flight of the day from BOS to MDW more likely to be cancelled?
Yes. Each airline's last BOS–MDW flight of the day was cancelled 4.1% of the time over the past year, against 1.2% for its earlier flights. If the last flight is cancelled, the next one is usually the following morning.
Related
- MDW → BOS (return)
- Boston Logan (BOS) delays by hour
- Flights into Chicago Midway (MDW)
- Southwest Airlines on-time record
- Connecting off this flight? Check the risk
Domestic flights by the airlines that report to the U.S. DOT, plus their regional partners. "On time" means arriving less than 15 minutes after schedule; cancelled and diverted flights count as not on time. Past performance is a guide, not a forecast. Method.