BTS DATA COMPLETE THROUGH JUNE 2026HISTORICAL ODDS · NOT LIVE FLIGHT STATUS
DelayOddsKnow the route before you book
OAK→MDW

Oakland, CA (OAK) to Chicago, IL (MDW) flight delay odds

84.4% of 482 official scheduled OAK-to-MDW flights arrived on time; 6.4% arrived at least 30 minutes late and 0.2% were cancelled during July 2025–June 2026.

Source: U.S. Bureau of Transportation Statistics · Reporting window: July 2025–June 2026 · Updated September 16, 2026

HISTORICAL ROUTE SIGNALLower disruption
84.4%arrived on time
6.4%30+ min late
0.2%cancelled
482scheduled flights
Based on July 2025–June 2026; on time means arrival less than 15 minutes late.
60+ minutes late1.7%all scheduled flights
120+ minutes late0.0%all scheduled flights
Diverted1.0%did not reach as scheduled
Average arrival-0.7 mincompleted flights

Which departure time was most reliable for OAK to MDW?

Among qualifying OAK-to-MDW departure window results, Early morning had the highest on-time rate: 88.5% of 243 flights. Night was lowest at 78.0% across 118 flights.

Departure windowFlightsOn time30+ minCancelled
Early morning24388.5%2.5%0.4%
Late morning8884.1%6.8%0.0%
Night11878.0%11.9%0.0%

Which weekday was most reliable for OAK to MDW?

Among qualifying OAK-to-MDW weekday results, Wednesday had the highest on-time rate: 88.4% of 69 flights. Saturday was lowest at 74.2% across 62 flights.

DayFlightsOn time30+ minCancelled
Monday6985.5%5.8%0.0%
Tuesday7085.7%5.7%0.0%
Wednesday6988.4%2.9%0.0%
Thursday6988.4%4.3%0.0%
Friday6987.0%4.3%0.0%
Saturday6274.2%8.1%1.6%
Sunday7481.1%13.5%0.0%

Which airline was most reliable for OAK to MDW?

Only Southwest Airlines met the OAK-to-MDW airline threshold: 84.4% of 482 scheduled flights arrived on time during July 2025–June 2026.

AirlineFlightsOn time30+ minCancelled
Southwest Airlines48284.4%6.4%0.2%

Which month was most reliable for OAK to MDW?

Among qualifying OAK-to-MDW month results, October 2025 had the highest on-time rate: 97.1% of 35 flights. June 2026 was lowest at 67.9% across 56 flights.

MonthFlightsOn time30+ minCancelled
July 20253591.4%2.9%0.0%
August 20253683.3%11.1%0.0%
September 20253491.2%0.0%0.0%
October 20253597.1%0.0%0.0%
November 20253369.7%12.1%0.0%
December 20253384.8%3.0%0.0%
January 20263287.5%6.2%0.0%
February 20262892.9%3.6%0.0%
March 20265581.8%3.6%1.8%
April 20265390.6%3.8%0.0%
May 20265284.6%5.8%0.0%
June 20265667.9%19.6%0.0%

What drove OAK to MDW delay minutes?

Late aircraft was the largest recorded OAK-to-MDW delay category, accounting for 43.3% of 2,302 BTS-attributed delay minutes during July 2025–June 2026.

Airline36.6%
Late aircraft43.3%
National airspace20.1%
Weather0.0%
Security0.0%
This is historical evidence, not a forecast.

Weather, schedules and operations change. For a trip you have already booked, use the airline or airport for live status.