Nonstop flights from Chicago to San Jose
Southwest Airlines flies this route twice a day.
MDWChicago Midway International
1,834 mi · 14 flights a week
SJCSan Jose Mineta International
When they leave
Chicago time10:10a8:50pFirst departure 10:10 AM, last 8:50 PM
Three in the morning, 10:10 AM to 10:20 AM, then three in the evening, 8:30 PM to 8:50 PM.
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Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Chicago to San Jose
Southwest Airlines is the only airline flying nonstop from Chicago to San Jose, twice a day on the Boeing 737 MAX 8 and Boeing 737-700.
The first arrival in San Jose is at 12:35 PM and the last at 11:20 PM. The flight covers 1,834 miles.
Flying back, San Jose to Chicago has 14 nonstop flights a week. O'Hare (ORD) also has nonstop flights to San Jose, 7 a week.
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Schedules as of Oct 9, 2026.