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Route Reliability

San Diego → Chicago

SAN–MDW · 1,728 miles · San Diego International Airport to Chicago Midway International Airport

80
Pretty Reliable
WanderNerd Reliability Score
78%
Arrive within 15 minutes
6 min
Average arrival delay
0.9%
Cancelled
1,067
Flights in the data

Data through May 2026.

Southwest Airlines is the only airline in this data on this route, arriving on time 78% of the time across 1,067 flights. No comparison to make.

What the data says

The late departure is the smart one here.

SAN–MDW flights departing between 9 PM–12 AM arrived on time 98% of the time, versus 59% between 6–9 PM.

Thursdays have been rough.

SAN–MDW flights arrived on time 89% of the time on Saturdays and just 72% on Thursdays. That gap is worth planning around.

Flights on this route

The breakdown

On-time by weekday
  • Mon76%(158 flights)
  • Tue79%(145 flights)
  • Wed83%(147 flights)
  • Thu72%(160 flights)
  • Fri74%(161 flights)
  • Sat89%(131 flights)
  • Sun76%(147 flights)
On-time by departure window
  • 6–9 AM90%(364 flights)
  • 9 AM–12 PM78%(208 flights)
  • 12–3 PM65%(132 flights)
  • 3–6 PM63%(136 flights)
  • 6–9 PM59%(123 flights)
  • 9 PM–12 AM98%(86 flights)
On-time trend by month
78%
May

Jun 69% → May 78% on time

On-time arrival percentage by month
MonthOn-time percentageFlights
June 202569%89
July 202570%91
August 202569%88
September 202574%86
October 202590%89
November 202585%81
December 202576%91
January 202681%67
February 202685%66
March 202681%98
April 202679%102
May 202678%101

Same trip, other airports

Keep nerding

Based on 1,067 historical flights, because apparently we checked. Historical flight data: U.S. Bureau of Transportation Statistics, June 2025 – May 2026. Data through May 2026. How we calculate this.