Cheap flights from San Jose to Chicago from $137

Traveling between San Jose and Chicago, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around San Jose. The main one is San Jose International and other nearby airports include San Francisco International, Oakland International, Sacramento International, Fresno Yosemite International, San Jose International, Stockton Metropolitan, Charles M. Schulz–Sonoma County, Merced Regional, Monterey Regional

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, Dane County Regional, South Bend International, General Mitchell International, Fort Wayne International, General Wayne A. Downing Peoria International, Quad City International, Central Illinois Regional, Kalamazoo/Battle Creek International, Muskegon County.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from San Jose, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from San Jose, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.