Cheap flights from Chicago to Costa Rica from $147

The cheapest month to fly to Costa Rica from Chicago is in September. Flight prices, which tend to average around $314, are often lower during this time because this is during the off-season. If you’re not able to fly to Costa Rica in September, then October is your next best option. Flight prices from Chicago to Costa Rica during October average around $376.

According to our data, Tuesday is the cheapest day to fly to Costa Rica from Chicago. The lowest ticket price found for a Tuesday departure recently was $512. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $702. These prices are subject to change though, so be sure to set up a Price Alert for flights to Costa Rica.

In the afternoon is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $498. Flying to Costa Rica in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly at noon, with an average ticket price of $664. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago O'Hare Intl to Liberia for the best Chicago - Costa Rica flight prices

You are more likely to see cheaper flights to Costa Rica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Costa Rica for around $516 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Costa Rica from Chicago for as low as $437 on momondo.

There are 3 cabin classes available to choose from on Chicago to Costa Rica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Air Canada, Spirit Airlines, and Frontier are the most popular carriers operating from Chicago to Costa Rica

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Costa Rica from Chicago according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Costa Rica. Keep in mind that there are 9 different airlines that fly to Costa Rica on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and Costa Rica have experienced a delay on any given week. The average delay length over the past 12 months has been 173 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

As of February 2026, 3 flights take off from Chicago and land in Costa Rica each day. The most common flight departure time for this route is 7:00AM, with 77% of daily flights taking off at noon.

As of February 2026, there are 27 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.