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 3h36m 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 SWA2986 | 12:13a | 3h36m | Tue–Thu |
| Southwest SWA2986 | 12:20a | 3h34m | Fri–Sat |
| Southwest SWA2986 | 12:29a | 3h35m | Mon |
| Southwest SWA2671 | 5:32a | 3h36m | Thu–Fri |
| Southwest SWA4295 | 5:36a | 3h36m | Sun |
| Southwest SWA2671 | 5:59a | 3h43m | Mon |
| Southwest SWA3816 | 10:43a | 3h41m | Wed |
| Southwest SWA3816 | 10:55a | 3h40m | Tue |
| Southwest SWA2986 | 11:58p | 3h32m | Sat |
SouthwestThe 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 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 Oakland to Chicago?
The nonstop flight from Oakland (OAK) to Chicago (MDW) takes about 3h36m 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 3h36m.