Cheap flights from Chicago to Costa Rica from $83
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Costa Rica departing on 8/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Costa Rica
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Costa Rica?
The cheapest month to fly to Costa Rica from Chicago is in July. Flight prices, which tend to average around $449, are often lower during this time because this is during the off-season. If you’re not able to fly to Costa Rica in July, then October is your next best option. Flight prices from Chicago to Costa Rica during October average around $552.
What is the cheapest day to depart on your flight to Costa Rica?
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 $581. 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 $823. These prices are subject to change though, so be sure to set up a Price Alert for flights to Costa Rica.
What is the cheapest time of day to depart on your flight to Costa Rica?
In the evening is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $436. Flying to Costa Rica in the evening is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly in the morning, with an average ticket price of $771. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Costa Rica flight route?
Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - Costa Rica flight prices
How far in advance should I book a flight to Costa Rica?
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 $599 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 $468 on momondo.
What cabin class options are available on Chicago to Costa Rica flights?
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.
What is the cheapest airline that flies from Chicago to Costa Rica?
Frontier, Spirit Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to Costa Rica
What airlines fly to Costa Rica?
United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Costa Rica from Chicago according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Costa Rica. Keep in mind that there are 8 different airlines that fly to Costa Rica on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Costa Rica on average per week?
As of July 2025, there are 2 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Wed, with 50% of flights taking off on this day.
Cheap Chicago to Costa Rica flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Costa Rica
When did momondo last update prices for flights from Chicago to Costa Rica?
Prices for flights from Chicago to Costa Rica are updated daily.
How many operators does momondo search for flights from Chicago to Costa Rica?
There are 8 operators available for flights from Chicago to Costa Rica as of July 2025.
How old do you have to be to fly from Chicago to Costa Rica?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Costa Rica.
What documentation or ID do you need to fly to Costa Rica?
The necessary travel and health documents for your Costa Rica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Costa Rica?
Based on momondo bookings for flights between Chicago and Costa Rica, the leading plane model is Boeing 737 MAX 8, making up 55.87% of the total bookings. Other popular models include Boeing 737-900 with 28.32%, Boeing 737-800 with 9.18%, and Boeing 737 MAX 9 with 4.85%.
Best airlines flying from Chicago to Costa Rica
Compare and see reviews for airlines that fly from Chicago to Costa Rica with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $274 | Free Cancellation | Rating 6.3 8,094 reviews | |||
| PriceFrom $317 | Free Cancellation | Rating 6.7 2,363 reviews | |||
| PriceFrom $345 | Free Cancellation | Rating 7.3 2,916 reviews | |||
| PriceFrom $367 | Free Cancellation | Rating 7.5 1,467 reviews | |||
| PriceFrom $438 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $444 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $477 | Free Cancellation | Rating 8.0 4,270 reviews | |||
| PriceFrom $480 | Free Cancellation | Rating 7.4 8,861 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Costa Rica?
Finding the right flight to Costa Rica from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Costa Rica quick and easy, saving you time and money.
Can I find flights from Chicago to Costa Rica with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Costa Rica flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Costa Rica?
Once all potential Chicago to Costa Rica flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Costa Rica right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Costa Rica, momondo offers a useful price alert feature which will track prices for flights to Costa Rica from Chicago and alert you when they change.