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Route Reliability

Oakland → Chicago

OAK–MDW · 1,844 miles · Oakland International Airport to Chicago Midway International Airport

92
Nerd Approved
WanderNerd Reliability Score
89%
Arrive within 15 minutes
2 min early
Average arrival delay
0.2%
Cancelled
459
Flights in the data

Data through May 2026.

Southwest Airlines is the only airline in this data on this route, arriving on time 89% of the time across 459 flights. No comparison to make.

What the data says

Morning flights do better here.

OAK–MDW flights departing between 6–9 AM arrived on time 94% of the time, versus 84% between 12–3 PM.

Saturday is the weak spot.

OAK–MDW flights arrived on time 95% of the time on Thursdays. On Saturdays: 82%.

It basically never cancels.

Out of 459 scheduled flights, only 0.2% were cancelled.

Flights on this route

The breakdown

On-time by weekday
  • Mon91%(64 flights)
  • Tue89%(63 flights)
  • Wed91%(65 flights)
  • Thu95%(64 flights)
  • Fri89%(64 flights)
  • Sat82%(60 flights)
  • Sun86%(73 flights)
On-time by departure window
  • 3–6 AM91%(187 flights)
  • 6–9 AM94%(50 flights)
  • 9 AM–12 PM85%(87 flights)
  • 12–3 PM84%(32 flights)
  • 3–6 PM—(9 flights)
  • 9 PM–12 AM89%(88 flights)
On-time trend by month
87%
May

Jun 91% → May 87% on time

On-time arrival percentage by month
MonthOn-time percentageFlights
June 202591%33
July 202594%34
August 202586%35
September 202591%34
October 202597%35
November 202581%31
December 202585%33
January 202688%32
February 202693%28
March 202687%53
April 202691%53
May 202687%52

Same trip, other airports

Keep nerding

Based on 459 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.