FlyOnSchedule

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

San Francisco International → Chicago Midway International

Data through July 2026 · Last updated October 18, 2026

On-time arrivals72.8%last 12 months
Avg delay when late41 minflights 15+ min late
Cancelled1.2%of scheduled flights
Flights485scheduled, 12 months

Over the last 12 months, 72.8% of San Francisco (SFO) to Chicago (MDW) flights arrived on time (485 scheduled flights). That is 4.8 points below the national average of 77.6%.

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

November has been the best month (88% on time) and Sunday the weakest day of the week (65%).

1.2% of flights were cancelled, versus 1.8% nationally.

SFO 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 72.8%41 min1.2% 485

80%+ good 70–79.9% fair <70% poor

Best time of day to fly SFO to MDW

On-time arrival % by scheduled departure hour (local time), 868 flights over 24 months.

Show the numbers
Departure hourOn timeCancelledFlights
5am–6am 89.7%2.4% 170
6am–7am 93.0%0.5% 215
7am–8am 90.9%1.8% 56
8am–9am 87.3%0.0% 71
9am–10am 75.6%0.0% 45
10am–11am 60.3%0.0% 122
12pm–1pm Limited data 18
1pm–2pm Limited data 22
11pm–12am 49.0%1.3% 149

Best day of the week

24 months, by day of departure.

Best month to fly

24 months, by calendar month.

Holiday travel on SFO 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) Limited data 13
Christmas & New Year (Dec 20 - Jan 3) 93.3% +15.9 pts 0.0% 30
Summer peak (Jun 15 - Aug 15) 72.1% -5.4 pts 1.1% 184
All other days77.4%—0.9%641

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).