FlyOnSchedule

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

Norman Y. Mineta San Jose International → Chicago Midway International

Data through July 2026 · Last updated October 18, 2026

On-time arrivals84.2%last 12 months
Avg delay when late32 minflights 15+ min late
Cancelled0.2%of scheduled flights
Flights519scheduled, 12 months

Over the last 12 months, 84.2% of San Jose (SJC) to Chicago (MDW) flights arrived on time (519 scheduled flights). That is 6.6 points above the national 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 (91% on time) and May the worst month (69%).

The cancellation rate was 0.2% (US average 1.8%).

SJC 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 84.2%32 min0.2% 519

80%+ good 70–79.9% fair <70% poor

Best time of day to fly SJC to MDW

On-time arrival % by scheduled departure hour (local time), 1,060 flights over 24 months.

Show the numbers
Departure hourOn timeCancelledFlights
6am–7am 93.7%0.0% 174
7am–8am 94.0%0.8% 119
8am–9am 91.8%0.0% 124
9am–10am 87.0%0.0% 54
10am–11am 78.1%0.0% 97
11am–12pm 74.1%0.4% 228
12pm–1pm Limited data 23
1pm–2pm 65.2%0.0% 46
2pm–3pm Limited data 18
6pm–7pm Limited data 28
10pm–11pm 94.0%0.0% 149

Best day of the week

24 months, by day of departure.

Best month to fly

24 months, by calendar month.

Holiday travel on SJC 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 14
Christmas & New Year (Dec 20 - Jan 3) 86.7% -0.9 pts 0.0% 30
Summer peak (Jun 15 - Aug 15) 78.0% -9.6 pts 0.4% 272
All other days87.5%—0.1%744

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).