OAK → MDWOakland to Chicago

live

Direct flights from Oakland (OAK) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 77% of the last 13 operated flights arrived within 15 minutes of schedule. The median arrival is 3 minutes early. 1 of the 13 tracked flights was cancelled. The nonstop covers 2,961 km, an estimated 4 hours 18 minutes in the air. Measured by Pro Flight Search from live flight boards at Oakland and Chicago. Updated 19 October 2026 at 07:42 UTC.

Today, OAK → MDW

Mon 19 Oct · local times
  1. · WN4320Southwest Airlines On schedule MDW 11:50scheduled

Checked OAK board 22:03 · MDW board 02:42

OAK Oakland disrupted · +63
MDW Chicago busy · +29
2,961 km · ~4h 18m est.
dep bank 05:10–23:557x weekly
Runs mixed · 1 airline · 7x weekly · nonstop
77% on time

of the last 13 operated OAK → MDW flights arrived within 15 minutes

Median arrival delay is −3 min. 1 of 13 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−3 minacross the last 13 operated legs
Flight time~4h 18mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled7.7%recent route rate · 1 of 13

The week

scheduled departures · origin local time
06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines

Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.

Who flies it

observed on the boards · 7 days
Southwest AirlinesWN77% on time

Flights WN3107 05:10 Su · WN4320 05:50 Mo Th Fr · WN1658 06:15 Tu We · WN3180 23:55 daily

History

operated legs · board outcomes
10-18WN3107dep +10 → arr−8
10-17WN3180dep +7 → arr−4
10-16WN3180cancelledCNX
10-16WN4320dep +16 → arr+17
10-15WN3180dep +38 → arr+29
10-15WN4320dep +16 → arr−4
10-14WN1658dep +24 → arr−1
10-14WN3180dep +28 → arr+3
10-13WN1658dep +12 → arr−24
10-13WN3180dep +15 → arr−7
10-12WN3180dep +32 → arr−3
10-12WN4320dep +31 → arr+2
10-11WN3180arrived−7

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
OAKOakland +63 min disrupted ⛅ mostly cloudy · W 10 kt Full OAK delay board →
MDWChicago +29 min busy 🌤 clear · SSW 7 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at MDW: 37% odds of a 15+ minute delay and around +9 min expected when it bites, measured from this route's own weather-matched delay history. See live delays → · Weather risk by airport →

How the Oakland to Chicago route actually runs

Pro Flight Search records official board updates for nonstop OAK to MDW flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.

Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure

Cite this data

Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.

Suggested citation

Pro Flight Search — Oakland (OAK) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/OAK-MDW
How we measure this →

OAK to MDW questions

Is OAK–MDW running on time right now?

Significant delay risk. The departure side at OAK is the weaker end, route health score 39/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on OAK–MDW?

Operators schedule morning departures around 05:10 and evening departures around 23:55 from OAK. Earlier flights typically land before destination-airport delays accumulate later in the day; check the MDW delay card to confirm conditions when you'd arrive.

How long is the flight from OAK to MDW?

Great-circle distance is 2,961 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 239–284 min gate-to-gate on this route.

How often does OAK–MDW fly?

Southwest Airlines runs the route with about 13 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.