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 4h8m 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 SWA2779 | 10:31a | 3h55m | Thu–Fri |
| Southwest SWA2779 | 10:38a | 4h10m | Tue–Wed |
| Southwest SWA2779 | 10:54a | 4h22m | Mon |
| Southwest SWA2779 | 11:16a | 4h2m | Sun |
| Southwest SWA2779 | 3:38p | 4h12m | Sat |
| Southwest SWA1413 | 8:40p | 4h6m | Fri |
| Southwest SWA3461 | 8:51p | 4h16m | Sun |
| Southwest SWA1413 | 9:00p | 4h5m | Wed |
| Southwest SWA1413 | 9:05p | 4h6m | Thu |
| Southwest SWA1413 | 9:17p | 4h16m | Tue |
| Southwest SWA1413 | 9:28p | 4h8m | Mon |
SouthwestThe 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 September 2026 from observed departures.
Route data updated September 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 4h8m 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 4h8m.