Cheap flights from Costa Rica to Chicago from $166

The month of January is, on average, the cheapest month to fly to Chicago from Costa Rica, with most prices found around $369. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Costa Rica to Chicago during October average around $412.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $428. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Costa Rica to Chicago for around $584.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Costa Rica to Chicago during this time can be as low as $463. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best Costa Rica - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Costa Rica when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $449 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Costa Rica for as low as $374 on momondo.

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

Spirit Airlines, Southwest, and Alaska Airlines are the most popular carriers operating from Costa Rica to Chicago

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Costa Rica 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 Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 10% of flights between Costa Rica and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 188 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. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

As of March 2026, 4 flights take off from Costa Rica and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 80% of daily flights taking off in the afternoon.

As of March 2026, 34 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.