MDW to BOS flight delays & on-time performance
Nonstop flights from Chicago Midway International Airport to Boston Logan International Airport · 861 miles · Aug 2025 – Jul 2026
No FAA-reported ground stops or delays at MDW or BOS right now. Individual flights can still be delayed by the airline; check with your airline for your flight.
Key facts
- Flights from Chicago (MDW) to Boston (BOS) arrived on time 67% of the time in Aug 2025 – Jul 2026, worse than the 78% national average.
- 1.2% were cancelled, and 11% arrived an hour or more late.
- Southwest Airlines is the only airline reporting nonstop flights on this route.
- Departures scheduled around 6am did best (95% on time); around 4pm did worst (33%).
- Saturday was the most reliable day to fly (77% on time) and Monday the least (60%).
- The largest source of delay minutes was air traffic control & airport congestion (36%).
Which airline is most on time from MDW to BOS?
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 | 67% | 1.2% | 22 min | 11.5% | 1,360 |
Best time of day to fly
On-time arrival rate by scheduled departure hour (local time).
- 5am94%36 flights
- 6am95%73 flights
- 7am90%132 flights
- 8am79%28 flights
- 9am85%183 flights
- 10am83%36 flights
- 11am52%26 flights
- 12pm56%126 flights
- 1pm54%113 flights
- 2pm54%90 flights
- 3pm48%74 flights
- 4pm33%64 flights
- 5pm62%71 flights
- 6pm64%164 flights
- 7pm50%109 flights
- 8pm53%16 flights
- 9pm72%18 flights
Best day of the week
On-time arrival rate by day of departure.
- Monday60%3.0% cancelled
- Tuesday68%0.0% cancelled
- Wednesday67%0.6% cancelled
- Thursday63%0.5% cancelled
- Friday68%0.5% cancelled
- Saturday77%1.6% cancelled
- Sunday65%1.9% cancelled
On-time trend by month
Why flights are late
Share of delay minutes by cause, as reported by airlines to the DOT.
- Air traffic control & airport congestion36%
- Late-arriving aircraft31%
- Airline (crew, maintenance, cleaning, fueling)29%
- Extreme weather2%
- Security1%
Why flights are cancelled
Share of cancellations by reason.
- Extreme weather81%
- Airline (crew, maintenance, cleaning, fueling)13%
- Air traffic control & airport congestion6%
- Security0%
MDW to BOS: common questions
- How often are MDW to BOS flights on time?
- 67% 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 Chicago to Boston cancelled?
- 1.2% of scheduled flights were cancelled (16 of 1,360).
- How long are typical delays?
- Across all flights the average arrival delay was 22 min (early arrivals count as zero). Flights that were late arrived 63 min behind schedule on average, and 11.5% of flights were an hour or more late.
- How long is taxi time at MDW?
- Flights on this route spent 15 min taxiing from the gate to takeoff on average.
Related routes
Return trip: BOS to MDW — 72% on time
More flights from Chicago
Data: U.S. DOT Bureau of Transportation Statistics, Aug 2025 – Jul 2026 (12 months). Latest month published by BTS: July 2026. Route: MDW → BOS, nonstop flights by US airlines that report to the DOT. How we calculate this.