Direct flights from San Jose to Chicago
14 nonstop flights a week on 1 airline. Zero layovers — one hop from SJC to MDW.
Flight time: about 3h44m nonstop
Which days does it fly?
When does it fly?
Departure times in San Jose local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA4357 | 10:16a | 3h44m | Thu–Fri |
| Southwest SWA4357 | 10:26a | 3h44m | Mon |
| Southwest SWA2812 | 10:52a | 3h41m | Sat |
| Southwest SWA4357 | 11:48a | 3h38m | Wed |
| Southwest SWA4357 | 11:55a | 3h51m | Tue |
| Southwest SWA4357 | 12:12p | 3h44m | Sun |
| Southwest SWA3886 | 11:02p | 3h45m | Mon, Fri |
| Southwest SWA3886 | 11:06p | 3h44m | Tue–Thu |
| Southwest SWA623 | 11:09p | 3h48m | Sun |
| Southwest SWA3886 | 11:21p | 3h38m | Sat |
Southwest
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The route
One hop: SJC → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from San Jose (SJC) to Chicago (MDW)
Norman Y. Mineta San Jose International Airport (SJC) has 14 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of SJC 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 San Jose to Chicago?
The nonstop flight from San Jose (SJC) to Chicago (MDW) takes about 3h44m in the air, based on recently observed nonstop departures.
How long does it take to drive from San Jose to Chicago?
Driving from San Jose to Chicago takes about 31h 44m behind the wheel — roughly 2,163 miles, or about 3 days of real driving. The nonstop flight takes about 3h44m.