Direct flights from Chicago Midway to Oakland
13 nonstop flights a week on 1 airline. Zero layovers — one hop from MDW to OAK.
Flight time: about 3h42m nonstop
Which days does it fly?
When does it fly?
Departure times in Chicago Midway local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA3366 | 10:14a | 3h57m | Wed |
| Southwest SWA3366 | 10:42a | 3h40m | Tue, Fri, Sun |
| Southwest SWA3366 | 11:04a | 3h39m | Thu |
| Southwest SWA3366 | 11:30a | 3h42m | Mon |
| Southwest SWA2221 | 1:49p | 3h42m | Sat |
| Southwest SWA4042 | 9:50p | 3h42m | Fri |
| Southwest SWA4042 | 10:11p | 4h1m | Mon |
| Southwest SWA2710 | 10:20p | 3h40m | Wed |
| Southwest SWA4042 | 10:23p | 3h40m | Thu |
| Southwest SWA4042 | 11:09p | 3h39m | Sun |
| Southwest SWA2710 | 11:38p | 3h53m | Tue |
Southwest
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The route
One hop: MDW → OAKDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Chicago Midway (MDW) to Oakland (OAK)
Chicago Midway International Airport (MDW) has 13 nonstop flights a week to Oakland (OAK), operated by Southwest. No layovers, no connections — one hop out of MDW and you're there.
This route flies every day of the week, so any travel day works. Route data updated July 2026 from observed departures.
Route data updated July 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Chicago Midway to Oakland?
The nonstop flight from Chicago Midway (MDW) to Oakland (OAK) takes about 3h42m in the air, based on recently observed nonstop departures.
How long does it take to drive from Chicago Midway to Oakland?
Driving from Chicago Midway to Oakland takes about 31h 11m behind the wheel — roughly 2,125 miles, or about 3 days of real driving. The nonstop flight takes about 3h42m.