FlyOnSchedule

Best Time to Fly PIT to MDW: On-Time Stats by Hour & Airline

Pittsburgh International → Chicago Midway International

Data through July 2026 · Last updated October 18, 2026

On-time arrivals79.6%last 12 months
Avg delay when late61 minflights 15+ min late
Cancelled1.1%of scheduled flights
Flights1,118scheduled, 12 months

1,118 flights were scheduled from Pittsburgh (PIT) to Chicago (MDW) in the last 12 months, and 79.6% of those that flew arrived on time, 2.0 points above the US average of 77.6%.

Southwest Airlines was the only reporting airline with regular flights on this route.

November has been the best month (89% on time) and Sunday the weakest day of the week (75%).

1.1% of flights were cancelled, versus 1.8% nationally.

PIT to MDW on-time performance by airline

Last 12 months. Airlines with fewer than 30 completed flights are marked “limited data”.

AirlineOn timeAvg delay when lateCancelledFlights
Southwest Airlines 79.6%61 min1.1% 1,118

80%+ good 70–79.9% fair <70% poor

Best time of day to fly PIT to MDW

On-time arrival % by scheduled departure hour (local time), 2,241 flights over 24 months.

Show the numbers
Departure hourOn timeCancelledFlights
5am–6am 96.0%0.0% 51
6am–7am 88.3%0.6% 336
7am–8am 81.6%0.8% 126
8am–9am 81.4%1.1% 185
9am–10am 94.4%0.0% 89
10am–11am 97.6%0.0% 41
11am–12pm Limited data 20
12pm–1pm 88.9%1.5% 137
1pm–2pm 82.6%0.8% 122
2pm–3pm 88.5%1.7% 178
3pm–4pm 75.0%0.9% 105
4pm–5pm 75.8%0.0% 121
5pm–6pm 77.0%1.6% 62
6pm–7pm 79.5%0.8% 123
7pm–8pm 74.5%0.4% 241
8pm–9pm 66.1%0.9% 224
9pm–10pm 63.8%0.0% 80

Best day of the week

24 months, by day of departure.

Best month to fly

24 months, by calendar month.

Holiday travel on PIT to MDW

On-time arrivals during holiday periods compared with all other days, last 24 months.

PeriodOn timevs other daysCancelledFlights
Thanksgiving week (Tue before to Mon after) 86.5% +3.9 pts 2.6% 38
Christmas & New Year (Dec 20 - Jan 3) 68.3% -14.3 pts 1.2% 83
Summer peak (Jun 15 - Aug 15) 77.2% -5.4 pts 1.0% 405
All other days82.6%—0.6%1,715

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).