Cheap flights from Chicago to San José

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How much should you expect to spend for a flight from Chicago to San José?

Flight prices from Chicago to San José change depending on demand and time of booking.

Pick a travel date to see today’s available fares.

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

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.

Flights from Chicago to San José - Juan Santamaria International

Explore flights from Chicago to San José your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Also interested in Costa Rica? Check out: Golfito, Liberia, Quepos, San José, Tamarindo.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.
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 3556 km 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.