BOS to MDW flight delays & on-time performance
Nonstop flights from Boston Logan International Airport to Chicago Midway International Airport · 861 miles · Aug 2025 – Jul 2026
No FAA-reported ground stops or delays at BOS or MDW right now. Individual flights can still be delayed by the airline; check with your airline for your flight.
Key facts
- Flights from Boston (BOS) to Chicago (MDW) arrived on time 72% of the time in Aug 2025 – Jul 2026, worse than the 78% national average.
- 1.9% were cancelled, and 9% arrived an hour or more late.
- Southwest Airlines is the only airline reporting nonstop flights on this route.
- Departures scheduled around 10am did best (96% on time); around 5pm did worst (37%).
- Wednesday was the most reliable day to fly (79% on time) and Sunday the least (66%).
- The largest source of delay minutes was late-arriving aircraft (57%).
Which airline is most on time from BOS to MDW?
Ranked by on-time arrival rate. Regional airlines fly under their partner's brand (e.g. SkyWest for Delta Connection or United Express).
| Airline | On time | Cancelled | Avg delay | 1 hr+ late | Flights |
|---|---|---|---|---|---|
| Southwest Airlines | 72% | 1.9% | 18 min | 9.3% | 1,361 |
Best time of day to fly
On-time arrival rate by scheduled departure hour (local time).
- 5am92%247 flights
- 7am93%138 flights
- 8am77%31 flights
- 9am91%54 flights
- 10am96%84 flights
- 11am86%29 flights
- 12pm82%50 flights
- 1pm71%134 flights
- 2pm81%90 flights
- 3pm54%89 flights
- 4pm60%58 flights
- 5pm37%79 flights
- 6pm45%183 flights
- 7pm45%31 flights
- 8pm35%27 flights
- 9pm44%17 flights
Best day of the week
On-time arrival rate by day of departure.
- Monday66%3.4% cancelled
- Tuesday72%2.3% cancelled
- Wednesday79%1.2% cancelled
- Thursday71%2.0% cancelled
- Friday74%0.9% cancelled
- Saturday79%2.2% cancelled
- Sunday66%1.4% cancelled
On-time trend by month
Why flights are late
Share of delay minutes by cause, as reported by airlines to the DOT.
- Late-arriving aircraft57%
- Air traffic control & airport congestion21%
- Airline (crew, maintenance, cleaning, fueling)20%
- Extreme weather2%
- Security0%
Why flights are cancelled
Share of cancellations by reason.
- Extreme weather69%
- Air traffic control & airport congestion19%
- Airline (crew, maintenance, cleaning, fueling)12%
- Security0%
BOS to MDW: common questions
- How often are BOS to MDW flights on time?
- 72% of flights arrived less than 15 minutes late in Aug 2025 – Jul 2026, compared with 78% for all US flights.
- How often are flights from Boston to Chicago cancelled?
- 1.9% of scheduled flights were cancelled (26 of 1,361).
- How long are typical delays?
- Across all flights the average arrival delay was 18 min (early arrivals count as zero). Flights that were late arrived 63 min behind schedule on average, and 9.3% of flights were an hour or more late.
- How long is taxi time at BOS?
- Flights on this route spent 17 min taxiing from the gate to takeoff on average.
Related routes
Return trip: MDW to BOS — 67% on time
More flights from Boston
Data: U.S. DOT Bureau of Transportation Statistics, Aug 2025 – Jul 2026 (12 months). Latest month published by BTS: July 2026. Route: BOS → MDW, nonstop flights by US airlines that report to the DOT. How we calculate this.