Cheap flights from Chicago to San José

Flights tailored to your budget

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How to estimate the price of a flight from Chicago to San José?

It depends. Prices for flights from Chicago to San José fluctuate based on several factors.

Select your dates to check current offers.

Checking fares across several nearby dates can help you see which days offer the best deals. Jetcost lets you track price changes and grab the best opportunities.

Flying between Chicago and San José? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

  • Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
  • Airports in San José: Besides San José - Juan Santamaria International, also consider Tobias Bolanos.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Chicago airports in a single search.

Flights from Chicago to San José - Juan Santamaria International

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 Ryanair, Easyjet, British Airways, Expedia, eDreams, and more.

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.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to San José.

How much does an airline ticket from Chicago to San José cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to San José.

How far is Chicago from San José?

Chicago is about 2210 mi from San José.

What are the airports in San José?

San José has another airport: Tobias Bolanos.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Costa Rica?

The most popular cities in Costa Rica according to our users' searches are: Golfito, Liberia, Quepos, San José, Tamarindo.

When should I book a flight from Chicago to San José?

This information is not available at the moment.

What is the cheapest month to fly from Chicago to San José?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to San José?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to San José?

This information is not available at the moment.