OAK → MDWOakland to Chicago

live

Direct flights from Oakland (OAK) to Chicago (MDW): 13 nonstop departures observed each week across 1 airline. 92% of the last 13 tracked flights arrived within 15 minutes of schedule. The median arrival is 4 minutes early. No cancellations were recorded across the 14 tracked flights. 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 1 November 2026 at 05:54 UTC.

Today, OAK → MDW

Sat 31 Oct · local times
  1. 22:55 WN2130Southwest Airlines On scheduleT2 MDW 05:05scheduled

Checked OAK board 22:03 · MDW board 00:54

OAK Oakland smooth · +9
MDW Chicago smooth · +0
2,961 km · ~4h 18m est.
dep bank 05:10–23:5513x weekly
Runs reliable · 1 airline · 13x weekly · nonstop
92% on time

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

Median arrival delay is −4 min. 0 of 14 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−4 minacross the last 13 arrivals
Flight time~4h 18mestimated from route distance
Weekly departures13x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 14

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 AirlinesWN100% 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
10-30WN3180dep +12 → arr−8
10-30WN4320dep +25 → arr+9
10-29WN3180dep +31 → arr+5
10-29WN4320dep +17 → arr−3
10-28WN1658dep +10 → arr−8
10-28WN3180dep +16 → arr−13
10-27WN1658dep +40 → arr−2
10-27WN3180dep +0 → arr+13
10-261I213dep +49 → arr+43
10-26WN3180departed+16
10-26WN4320dep +5 → arr−20
10-25WN3107dep +5 → arr−11
10-25WN3180dep +15 → arr−4
10-24WN3180arrived−23

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 +9 min smooth 🌤 mostly cloudy · N 0 kt Full OAK delay board →
MDWChicago +0 min smooth 🌤 overcast · SE 3 kt Full MDW delay board →

Weather lens

Conditions are tightest at OAK: a 43% chance of a 15+ minute delay. In this weather, the more delayed of the two airports is typically about +8 min. Both figures come from the two airports' delay records in similar weather. 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?

Smooth skies ahead. The departure side at OAK is the weaker end, route health score 93/100. 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.