Nonstop flights from San Jose to Chicago

Southwest Airlines flies this route twice a day.

SJCSan Jose Mineta International

1,834 mi · 14 flights a week

MDWChicago Midway International

SJCMDW

When they leave

San Jose time

6:10a11:00pFirst departure 6:10 AM, last 11:00 PM

Three in the morning, 6:10 AM to 11:20 AM, then one evening flight at 11:00 PM.

Every flight

Earliest first

6:10 AM→12:20 PMSouthwest AirlinesBoeing 737 MAX 8Sun
9:55 AM→4:00 PMSouthwest AirlinesBoeing 737Tue, Wed, Sat
11:20 AM→5:30 PMSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
11:00 PM→5:00 AM⁺¹Southwest AirlinesBoeing 737 MAX 8Daily

Schedules last checked Sep 19, 2026. Times are local.

Flying from San Jose to Chicago

Southwest Airlines is the only airline flying nonstop from San Jose to Chicago, twice a day on the Boeing 737 MAX 8, Boeing 737 and Boeing 737-700.

The first arrival in Chicago is at 12:20 PM and the last at 5:00 AM the next day. The flight covers 1,834 miles.

Flying back, Chicago to San Jose has 14 nonstop flights a week. From San Jose, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 14 a week.

Return flights

Chicago to San JoseView

Every Chicago airport

All San Jose to Chicago flightsView

Find the cheapest day to fly from San Jose to Chicago.

Schedules as of Oct 9, 2026.