Direct flights from Oakland to Chicago
13 nonstop flights a week on 1 airline. Zero layovers — one hop from OAK to MDW.
Flight time: about 3h42m nonstop
Which days does it fly?
When does it fly?
Departure times in Oakland local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA3059 | 12:08a | 3h43m | Thu, Sat, Sun |
| Southwest SWA3059 | 12:15a | 3h38m | Wed |
| Southwest SWA3059 | 12:42a | 3h41m | Tue |
| Southwest SWA3059 | 1:03a | 3h48m | Mon |
| Southwest SWA3059 | 1:42a | 3h44m | Fri |
| Southwest SWA2211 | 5:22a | 3h37m | Sun |
| Southwest SWA2744 | 5:22a | 3h46m | Mon, Thu |
| Southwest SWA2744 | 5:42a | 3h45m | Fri |
| Southwest SWA2761 | 6:09a | 3h37m | Wed |
| Southwest SWA2761 | 6:18a | 3h41m | Tue |
Southwest
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The route
One hop: OAK → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Oakland (OAK) to Chicago (MDW)
Oakland San Francisco Bay Airport (OAK) has 13 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of OAK 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 Oakland to Chicago?
The nonstop flight from Oakland (OAK) to Chicago (MDW) takes about 3h42m in the air, based on recently observed nonstop departures.
How long does it take to drive from Oakland to Chicago?
Driving from Oakland to Chicago takes about 31h 11m behind the wheel — roughly 2,125 miles, or about 3 days of real driving. The nonstop flight takes about 3h42m.