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