Cheap flights from Chicago to Costa Rica

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Compare flights from Chicago to Costa Rica

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Where in Costa Rica would you like to go?

There are lots of destinations to choose from when you're planning your trip from Chicago to Costa Rica.

Flying from Chicago to Costa Rica

The things to know before you go.
Cheapest plane ticket found$270
Cheapest month to flyApril
Average flight time5 hrs, 15 mins
Places to go13
Most popular airlineAmerican Airlines
Average flights per week12

Cheapest time to fly from Chicago to Costa Rica

Looking for the lowest ticket prices to Costa Rica from Chicago? We can help you pick the cheapest month to fly.

Chicago to Costa Rica flight deals

Looking for a cheap plane ticket from Chicago to Costa Rica? Whether you're looking for a direct flight, round-trip flight or one-way ticket, we've got you.

Flights from Chicago to Costa Rica FAQs

The cheapest month to fly from Chicago to Costa Rica is April. See if any of these flights in April suit you.
We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago to Costa Rica is Chicago to San Jose Juan Santamaria. You can buy a ticket to fly this route from $270.

Take a look at Chicago to San Jose Juan Santamaria flights.
The average flight time from Chicago to Costa Rica is 5 hours and 19 minutes.
Looking at the year ahead, the cheapest airline flying to Costa Rica from Chicago is Spirit Airlines.

Explore Spirit Airlines flight ticket options today. 

If this airline doesn't suit you, the second cheapest airline is United.

How to find cheap flights from Chicago to Costa Rica

To find affordable flights from Chicago to Costa Rica, use Skyscanner to compare options across major airlines and online travel agents. Use our Whole Month view to spot the best dates and identify January as the cheapest month. Set up Price Alerts to stay updated on fare changes. Consider flying from nearby airports to secure more savings and filter for direct routes to shorten your journey to around 5 hours and 14 minutes. With an average of 40 flights per week, you have plenty of options to pick from. Finally, explore flexible ticket options or add travel insurance to protect your plans.

Other routes from the United States to Costa Rica

When planning a trip from the United States to Costa Rica, Skyscanner provides numerous flight options in various cities. For instance, from New York, travelers can explore direct and connecting routes to enjoy the scenic beauty of Costa Rica. Flights from Los Angeles often combine flexibility and convenient schedules. If you're departing from Miami, anticipate a range of options with relatively short durations. For those in Houston, there are several connections to choose from. Skyscanner helps you compare flights, ensuring you find the best route to your destination. To start planning, simply enter your departure city and Costa Rica as your destination.

Costa Rica destinations you can fly to from Chicago

From Chicago, you can practically fly to San Jose and Liberia in Costa Rica. San Jose serves as the capital city and hub for exploring the country's history and nearby natural reserves. Liberia, the capital of Guanacaste province, acts as a gateway to Pacific beaches, rainforests, and attractions like the Liberia Carnival and Guanacaste Day festival. Visit Rincon de la Vieja National Park for outdoor activities. Expect cultural festivals in Liberia and convenient access to national parks from San Jose. Both cities offer a blend of urban amenities and access to Costa Rica's famed natural beauty.

The cheapest city in Costa Rica to catch a flight to

For travelers flying from Chicago, San Jose is the cheapest city in Costa Rica to reach. When planning your itinerary, consider exploring attractions such as the Costa Rican National Museum, the local markets, and museums showcasing both traditional and contemporary art. Additionally, take advantage of free walking tours to discover more of the city's culture and history. If you're interested in nightlife, visit districts like San Pedro and Barrio Escalante.

The weather in Costa Rica

Costa Rica's tropical climate features two main seasons that you should be aware of when planning a visit. The dry season, from December to April, offers hot conditions with temperatures between 77°F and 82°F. This is ideal for beach visits. The rainy season, from May to November, brings warm weather with frequent afternoon showers and temperatures from 68°F to 90°F. Inland and mountainous regions are milder and more humid compared to the coastal areas. While hurricanes can occur on the Caribbean coast, they are rare. For safety, monitor local forecasts and consider visiting during the dry season for optimal weather.


Prices shown on this page are estimated lowest prices only. Found in the last 45 days.