Chicago (MDW) → San Jose (SJC)
Southwest Airlines operates nonstop flights from Chicago (MDW) to San Jose (SJC). The nonstop flight takes around ~3h 41m, covering 1,833 miles (2,950 km). Updated 31 May 2026.
MDW
→
SJC
Round trip
1 adult
Economy
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Frequently asked questions
Is there a direct flight from Chicago to San Jose?
Yes, Southwest Airlines operates nonstop flights from Chicago (MDW) to San Jose (SJC).
Which airlines fly direct from Chicago to San Jose?
Southwest Airlines operates nonstop flights from Chicago to San Jose.
How long is the flight from Chicago to San Jose?
The nonstop flight from Chicago to San Jose takes ~3h 41m (approximately 2950 km).