How much is a flight from San Jose to Chicago?

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

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the San Jose - Chicago route.

Planning flights between San Jose and Chicago? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in San Jose: San Jose is the only airport in this city.
• Airports in Chicago: Chicago features 3 airports - Midway, O'Hare, Rockford.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Find flights from San Jose to Chicago that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from the best airlines and travel agencies.

Other popular destinations

Interested in United States? These cities are also in demand: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.