Cheap flights from San José to Chicago from $294

Travelers frequently search for route combinations, such as San José and Los Angeles, New York, Washington, D.C., Atlanta, Charlotte, San Francisco, Orlando, Fort Lauderdale, Boston, Raleigh, Cincinnati, Tampa, San Juan, Dallas, Denver, Miami, Portland, Seattle, Asheville, Las Vegas.

Travelers frequently search for route combinations, such as Chicago and Mexico City, New York, Guadalajara, Dallas, Houston, Atlanta, Los Angeles, Morelia, Orlando, Philadelphia, León, Tampa, San Francisco, Miami, Denver, Phoenix, Seattle, Monterrey, Las Vegas, Washington, D.C..

The main airport in San José is Juan Santamaría International. It is also served by Daniel Oduber Quirós International, Quepos La Managua, Limón International, Fortuna Arenal, Tortuguero.

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, South Bend International, General Mitchell International, Dane County Regional, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, University of Illinois Willard, Muskegon County.

Currently, you can fly between San José and Chicago with Frontier Airlines, Volaris, Avianca, JetBlue Airways, Copa Airlines.

If you don’t have specific dates for your trip between San José and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between San José 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 José. The main one is Juan Santamaría International and other nearby airports include Daniel Oduber Quirós International, Quepos La Managua, Limón International, Fortuna Arenal, Tortuguero

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, South Bend International, General Mitchell International, Dane County Regional, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, University of Illinois Willard, Muskegon County.