Cheap flights from Chicago to San Jose
From 329 USD — compare hundreds of airlines
Live fares from 100+ sites — free, with no hidden fees.
About this route
Compare flights from Chicago to San Jose, a about 2,958 km route (around 4h 12m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as American Airlines, Alaska Airlines, Southwest Airlines operate this route.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Chicago to San Jose?
Prices vary by season; use the price calendar to find the cheapest month.
How long is the flight from Chicago to San Jose?
A nonstop flight takes about 4h 12m and covers around 2,958 km. Connecting itineraries take longer.
Are there direct flights from Chicago to San Jose?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Chicago to San Jose?
American Airlines, Alaska Airlines, Southwest Airlines operate this route, among others. Compare them all in the results.
When should I book Chicago–San Jose flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.
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Chicago → San Jose · Live fares from 100+ sites — free, with no hidden fees.