FlyOnSchedule

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

Chicago Midway International → Portland International

Data through July 2026 · Last updated October 18, 2026

On-time arrivals61.6%last 12 months
Avg delay when late52 minflights 15+ min late
Cancelled1.0%of scheduled flights
Flights683scheduled, 12 months

683 flights were scheduled from Chicago (MDW) to Portland (PDX) in the last 12 months, and 61.6% of those that flew arrived on time, 16.0 points below the US 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 (74% on time) and March the worst month (52%).

The cancellation rate was 1.0% (US average 1.8%).

MDW to PDX 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 61.6%52 min1.0% 683

80%+ good 70–79.9% fair <70% poor

Best time of day to fly MDW to PDX

On-time arrival % by scheduled departure hour (local time), 1,283 flights over 24 months.

Show the numbers
Departure hourOn timeCancelledFlights
7am–8am 68.6%0.0% 70
8am–9am 79.1%0.0% 116
9am–10am 75.0%0.0% 76
10am–11am 77.2%0.6% 168
11am–12pm Limited data 9
12pm–1pm Limited data 9
1pm–2pm Limited data 1
2pm–3pm 68.6%1.4% 71
3pm–4pm 69.3%0.0% 88
4pm–5pm 62.2%0.0% 157
5pm–6pm Limited data 29
6pm–7pm 66.7%0.0% 48
7pm–8pm 63.6%0.0% 55
8pm–9pm 63.0%0.0% 154
9pm–10pm 49.3%3.3% 151
10pm–11pm 54.3%0.0% 81

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 PDX

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) Limited data 14
Christmas & New Year (Dec 20 - Jan 3) 50.0% -19.6 pts 0.0% 30
Summer peak (Jun 15 - Aug 15) 57.6% -12.0 pts 0.6% 346
All other days69.6%—0.5%893

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).