Cheap flights from San Jose to Chicago
From 151 USD — compare hundreds of airlines
About this route
Compare flights from San Jose to Chicago, 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, Southwest Airlines operate this route.
Airlines on this route
FAQ
What's the cheapest month to fly San Jose to Chicago?
Prices vary by season; use the price calendar to find the cheapest month.
How long is the flight from San Jose to Chicago?
A nonstop flight takes about 4h 12m and covers around 2,958 km. Connecting itineraries take longer.
Are there direct flights from San Jose to Chicago?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from San Jose to Chicago?
American Airlines, Southwest Airlines operate this route, among others. Compare them all in the results.
When should I book San Jose–Chicago 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.