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WanderNerd

Route Reliability

Chicago → Oakland

MDWOAK · 1,844 miles · Chicago Midway International Airport to Oakland International Airport

65
Usually Fine
WanderNerd Reliability Score
66%
Arrive within 15 minutes
15 min
Average arrival delay
1.3%
Cancelled
460
Flights in the data

Data through May 2026.

Southwest Airlines is the only airline in this data on this route, arriving on time 66% of the time across 460 flights. No comparison to make.

What the data says

Morning flights do better here.

MDW–OAK flights departing between 9 AM–12 PM arrived on time 79% of the time, versus 48% between 9 PM–12 AM.

Monday is the weak spot.

MDW–OAK flights arrived on time 71% of the time on Fridays. On Mondays: 57%.

Flights on this route

The breakdown

On-time by weekday
  • Mon57%(63 flights)
  • Tue70%(64 flights)
  • Wed66%(64 flights)
  • Thu62%(63 flights)
  • Fri71%(65 flights)
  • Sat70%(60 flights)
  • Sun64%(74 flights)
On-time by departure window
  • 6–9 AM65%(117 flights)
  • 9 AM–12 PM79%(107 flights)
  • 12–3 PM70%(30 flights)
  • 3–6 PM66%(100 flights)
  • 6–9 PM56%(36 flights)
  • 9 PM–12 AM48%(63 flights)
On-time trend by month
73%
May

Jun 77% → May 73% on time

On-time arrival percentage by month
MonthOn-time percentageFlights
June 202577%34
July 202559%34
August 202578%37
September 202577%34
October 202549%35
November 202568%31
December 202539%33
January 202675%32
February 202675%28
March 202664%50
April 202657%53
May 202673%52

Based on 460 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.