Cheap flights from Costa Rica to Chicago from $155
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Costa Rica to Chicago departing on 11/7. 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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Spirit Airlines flights from Costa Rica to Chicago
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United Airlines flights from Costa Rica to Chicago
Our best United Airlines deals on Costa Rica to Chicago flight tickets
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How to get the cheapest flight ticket from Costa Rica to Chicago
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 Chicago?
The month of August is, on average, the cheapest month to fly to Chicago from Costa Rica, with most prices found around $413. If you’re not able to fly to Chicago in August, then July is your next best option. Flight prices from Costa Rica to Chicago during July average around $433.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $400. 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 $634.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Costa Rica to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $602.
What is the cheapest Costa Rica to Chicago flight route?
Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best Costa Rica - Chicago flight prices
How far in advance should I book a flight to Chicago?
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 $481 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 $406 on momondo.
What cabin class options are available on Costa Rica to Chicago flights?
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.
What is the cheapest airline that flies from Costa Rica to Chicago?
Viva, Spirit Airlines, and Southwest are the most popular carriers operating from Costa Rica to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Costa Rica according to our data. United Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Costa Rica to Chicago on average per week?
As of July 2025, 2 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Wed, with 50% of weekly flights taking off on this day.
Cheap Costa Rica to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Costa Rica to Chicago
When did momondo last update prices for flights from Costa Rica to Chicago?
Prices for flights from Costa Rica to Chicago refresh daily.
How many operators does momondo search for flights from Costa Rica to Chicago?
The number of operators available for flights from Costa Rica to Chicago is 7 as of July 2025.
How old do you have to be to fly from Costa Rica to Chicago?
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 Costa Rica to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Costa Rica to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Costa Rica to Chicago is Boeing 737 MAX 8, representing 60.69% of all bookings. The subsequent popular models are Airbus A320-100/200 at 8.02%, Airbus A320neo at 6.87%, and Airbus A330-300 at 6.11%.
Best airlines flying from Costa Rica to Chicago
Compare and see reviews for airlines that fly from Costa Rica to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $249 | Free Cancellation | Rating 6.7 2,363 reviews | |||
| PriceFrom $266 | Free Cancellation | Rating 6.3 8,094 reviews | |||
| PriceFrom $314 | Free Cancellation | Rating 7.5 1,467 reviews | |||
| PriceFrom $425 | Free Cancellation | Rating 8.0 4,270 reviews | |||
| PriceFrom $434 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $436 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $446 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Costa Rica to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Costa Rica.
Can I find flights from Costa Rica to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Costa Rica on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Costa Rica to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Costa Rica to Chicago.
I’m not ready to book a flight from Costa Rica to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Costa Rica. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.