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

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

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.

Exploring all airports near Chicago and San José

Checking all the airports available in the area can give you more departure and arrival options for your trip.

• Airports in Chicago: 3 different airports operate in Chicago - Midway, O'Hare, Rockford.
• Airports in San José: Try also checking Tobias Bolanos along with San José - Juan Santamaria International.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Filter and compare flights from Chicago to San José

Jetcost helps you manage complex searches with simple filters. Sort by airline, duration, number of stops, or even time windows for outbound and return flights.

Other popular destinations

Want more ideas for your trip to Costa Rica? Check these: Golfito, Liberia, Quepos, San José, Tamarindo.

Advanced filters help you skip long layovers or inconvenient times. The “airlines” filter is handy if you want to collect miles or prefer a certain onboard experience.