What’s the cost of a flight from San José to Chicago?

Prices vary based on date, airline, and availability. Compare several options if you're flying between San José and Chicago.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which airports are most convenient between San José and Chicago?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in San José: Another nearby option is Tobias Bolanos.
• Airports in Chicago: In Chicago you can fly to/from 3 airports - Midway, O'Hare, Rockford.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Find the best flight from San José to Chicago

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Ryanair, Easyjet, British Airways, and more.

Other popular destinations

Searching for flights to United States? Travelers also looked at: Atlanta, Los Angeles, Miami, New York City, Orlando.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for San José – Chicago flights.