How much is 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.

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 Chicago - San José route.

Which departure and arrival airports are available?

Between Chicago and San José, flight options may depend on the combination of airports available.

• Airports in Chicago: Chicago is connected by 3 airports - Midway, O'Hare, Rockford.
• Airports in San José: Another alternative is Tobias Bolanos.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Customize your flight from Chicago to San José

Jetcost allows you to filter by travel dates, duration, layovers, carriers, and booking providers. You’ll find direct and connecting flights, one-way or round-trip, from the best airlines and travel agencies.

Other popular destinations

Thinking about Costa Rica? You might also consider: Golfito, Liberia, Quepos, San José, Tamarindo.

You can sort results by price, duration, or departure time to find the best option for you. When available, results always include both low-cost and traditional airlines.