MDW → OAKChicago to Oakland

live

Direct flights from Chicago (MDW) to Oakland (OAK): 11 nonstop departures observed each week across 1 airline. 100% of the last 13 tracked flights arrived within 15 minutes of schedule. The median arrival is 16 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 Chicago and Oakland. Updated 2 November 2026 at 07:53 UTC.

Today, MDW → OAK

Mon 2 Nov · local times
  1. 10:05 WN3174Southwest Airlines On scheduleGate B7 ·
  2. 21:55 WN2990Southwest Airlines Sched 21:55Departure not confirmed by the board ·

Checked MDW board 01:53 · OAK board 22:03

MDW Chicago heavy · +41
OAK Oakland heavy · +31
2,961 km · ~4h 18m est.
dep bank 10:05–21:3011x weekly
Runs reliable · 1 airline · 11x weekly · nonstop
100% on time

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

Median arrival delay is −16 min. 0 of 14 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−16 minacross the last 13 arrivals
Flight time~4h 18mestimated from route distance
Weekly departures11x1 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 WN4280 varies Mo Tu We Th Fr Su · WN818 20:35 Tu We · WN4293 21:30 Mo Th Fr

History

operated legs · board outcomes
11-01WN2990departed+40
11-01WN3174dep +5 → arr−14
10-31WN2865dep +1 → arr−6
10-30WN4280dep +19 → arr+9
10-30WN4293dep −1 → arr−23
10-29WN4280dep +1 → arr−19
10-29WN4293dep +26 → arr+1
10-28WN4280dep −1 → arr−16
10-28WN818dep −4 → arr−19
10-27WN4280dep +40 → arr−34
10-27WN818dep −5 → arr−25
10-26WN4280dep +8 → arr−17
10-26WN4293dep +30 → arr+12
10-25WN2015arrived+4

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
MDWChicago +41 min heavy 🌤 overcast · S 5 kt Full MDW delay board →
OAKOakland +31 min heavy 🌤 clear · ESE 7 kt Full OAK 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 Chicago to Oakland route actually runs

Pro Flight Search records official board updates for nonstop MDW to OAK 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: Chicago (MDW) to Oakland (OAK) route reliability, measured from operated flights on official airport boards.

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

MDW to OAK questions

Is MDW–OAK running on time right now?

Some delays possible. The departure side at MDW is the weaker end, route health score 52/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on MDW–OAK?

Operators schedule evening departures around 20:35 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the OAK delay card to confirm conditions when you'd arrive.

How long is the flight from MDW to OAK?

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 MDW–OAK fly?

Southwest Airlines runs the route with about 11 flights a week (sun, mon, tue, wed, thu, fri). Since one carrier owns the route, a single disruption tends to ripple through the day.