How much is a ticket from San José Tobías Bolaños to Chicago?

Depending on when you travel and how far in advance you book, fares between San José and Chicago can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Planning flights between San José 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 José: San José - Tobias Bolanos 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.

Flight filters for the route San José Tobías Bolaños – Chicago

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Las Vegas, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.