$121 Find Cheap Flights from Chicago to Costa Rica

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Costa Rica departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Costa Rica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
San José
San José2 stops$348
Liberia
Liberia2 stops$448
San José
San José2 stops$348
Liberia
Liberia2 stops$448

Book Cheap Chicago to Costa Rica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Costa Rica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Costa Rica

Sat, Feb 14 - Sat, Feb 21
Spirit Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m2 stops
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m2 stops
$348Spirit Airlines
Mon, Feb 2 - Thu, Feb 5
Multiple Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m1 stop
Multiple Airlines Logo
12:33 pm - 10:35 am
SJO
-
ORD
22h 02m1 stop
$349Multiple Airlines
Sun, Jan 25 - Tue, Feb 3
American Airlines Logo
5:30 pm - 10:30 pm
ORD
-
SJO
5h 00mnonstop
American Airlines Logo
8:00 am - 6:10 pm
SJO
-
ORD
10h 10m1 stop
$350American Airlines
Sat, Feb 28 - Sat, Mar 7
Multiple Airlines Logo
12:06 pm - 12:22 pm
ORD
-
SJO
24h 16m1 stop
Multiple Airlines Logo
8:05 pm - 10:33 am
SJO
-
ORD
38h 28m2 stops
$351Multiple Airlines
Sun, Feb 1 - Fri, Feb 6
Multiple Airlines Logo
5:15 am - 6:55 pm
ORD
-
SJO
13h 40m2 stops
Multiple Airlines Logo
1:30 pm - 11:47 pm
SJO
-
ORD
10h 17m1 stop
$352Multiple Airlines
Fri, Jan 30 - Wed, Feb 4
American Airlines Logo
9:10 pm - 12:12 pm
ORD
-
LIR
15h 02m2 stops
American Airlines Logo
3:13 pm - 7:22 am
LIR
-
ORD
16h 09m2 stops
$448American Airlines
Fri, Feb 27 - Tue, Mar 3
GOL Logo
8:18 am - 1:32 pm
ORD
-
LIR
5h 14mnonstop
GOL Logo
3:29 pm - 8:38 am
LIR
-
ORD
17h 09m1 stop
$455GOL
Fri, Jan 30 - Thu, Feb 5
Air Canada Logo
8:45 pm - 2:45 pm
ORD
-
LIR
18h 00m1 stop
Air Canada Logo
3:55 pm - 1:01 pm
LIR
-
ORD
21h 06m2 stops
$456Air Canada
Mon, Mar 23 - Thu, Apr 2
Air Canada Logo
7:15 am - 1:50 pm
ORD
-
LIR
31h 35m1 stop
Air Canada Logo
2:55 pm - 1:00 pm
LIR
-
ORD
21h 05m1 stop
$457Air Canada
Fri, Feb 27 - Tue, Mar 3
GOL Logo
5:00 am - 12:32 pm
ORD
-
LIR
7h 32m1 stop
GOL Logo
3:29 pm - 9:45 am
LIR
-
ORD
18h 16m1 stop
$460GOL
Booking Insights

KAYAK's insights & trends for Chicago to Costa Rica flights

Get data-powered insights and trends into flights from Chicago to Costa Rica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Costa Rica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Costa Rica from Chicago O'Hare Intl Airport found in the last 72 hours was to San José, at $357 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San José (SJO), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $357.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Costa Rica?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $495 on average.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Costa Rica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Costa Rica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Costa Rica is October, when tickets cost $356 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $686 and $611 respectively.

What’s the cheapest day of the week to fly from Chicago to Costa Rica?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Costa Rica clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Costa Rica, look for departures on Tuesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Costa Rica, Thursday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Costa Rica?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Costa Rica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Costa Rica, you should book around 2 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$121
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago O'Hare Airport to San José

FAQs - booking Costa Rica flights

  • Are there any onsite hotels at Costa Rican airports?

    There are various hotels within and near SJO and LIR where passengers landing late at the airport can spend the night. Hampton Inn & Suites by Hilton San Jose Airport, situated approximately 0.7 miles from SJO, is your best bet. In addition, the hotel offers hotel shuttle transfers. On the other hand, if you are landing at LIR, you can make a reservation at Hilton Garden Inn Liberia, found 0.7 miles away from the airport.

  • How is parking at ORD?

    Passengers who want to leave their cars at the airport while flying out can use the multiple parking lot options available at Chicago O’hare International Airport. You can leave your car at the offsite parking lots, which are more affordable than onsite parking lots. Those who wish to leave their cars at the airport for a long can use the long-term parking lot and Economy Lot F. Alternatively, if you want to park short-term, you can take advantage of the hourly and daily parking lots found at the airport’s terminal parking.

  • Does ORD offer any pet facilities?

    ORD features three outdoor pet relief areas that passengers flying through the airport with their furry friends can utilize to make them comfortable before their flights to Costa Rica. The relief areas are located at terminals 1, 2 and 5.

  • Can I have accessibility services at Costa Rican airports?

    Upon request, you can have access to extra assistance and wheelchair services at LIR and SJO if you are flying with a companion with reduced mobility. However, you need to contact your airline earlier before travel date to have the services arranged.

  • How does KAYAK find such low prices on flights from Chicago to Costa Rica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Costa Rica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Costa Rica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Costa Rica is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Costa Rica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Costa Rica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Costa Rica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Costa Rica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Costa Rica?

    The cheapest time of day to fly to Costa Rica is generally in the evening, when round-trip flights cost $510 on average. Morning departures are around 26% more expensive than evening flights, on average. The most expensive time of day to fly to Costa Rica is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $664.

Top tips for finding cheap flights to Costa Rica

  • Juan Santamaría International Airport (SJO), situated approximately 6.2 miles away from San Jose in Costa Rica, is the main airport in the city, serving many international and domestic flights. However, from Chicago O’Hare International Airport (ORD), you can also land at Daniel Oduber International Airport (LIR), which is approximately 8 miles from Liberia, Costa Rica.
  • If you want to freshen up at Chicago O’Hare International Airport (ORD) before boarding your flight to Costa Rica, there are shower amenities in terminals 1 and 3. These shower facilities are found at the American Airlines Admirals Club, United Polaris Lounge and Hilton Athletic Club. However, if you want to access these facilities, you need to have a lounge pass.
  • ORD features a family lounge with a play area where your kids can burn off steam before boarding their flights to Costa Rica. It is equipped with climbing structures, toys and games and is located in the Main hall in terminal 2. Additionally, it features comfortable benches with charging stations where parents can sit and monitor their kids.
  • LIR and SJO feature a few lounges where passengers can unwind and relax upon arrival at the airports. These lounges offer exceptional services such as meals, drinks, entertainment, comfortable seats, internet access and flight information monitor. However, you need to have a lounge pass if you want to take advantage of these services and amenities.
  • If you are flying from ORD to Costa Rica, you can opt for one-stop flight options or airlines offering multiple layover options. Fly with Spirit Airlines, Copa Airlines, American Airlines and Jetblue Airlines, offering short layovers with stops at DFW, FTY, JFK, MIA and FLL airports.

Reviews of the top 5 airlines serving from Chicago to Costa Rica

 
Need help choosing which airline to fly with from Chicago to Costa Rica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
Copa AirlinesOverall score based on 1559 reviews
7.4Comfort
8.1Crew
6.8Entertainment
7.8Boarding
6.8Food
Airline reviews

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

2.0 MediocreAnonymous, Dec 2025
LAS - PTY
Read more Copa Airlines reviews

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Avianca has transitioned from full service legacy airline to "low cost" but has now became a strange hybrid (minimum leg space, started offering business class in domestic flights again, charges passenger for printing boarding pass, etc.). National and international coverage and destinations are really wide but service is not at its best

Deplaning was a mess, I sat in business (seats are horrible) and the front door had a problem so we had to deplane from the rear exit. The stairs were not tall enough to reach so there was a large step down from the plane to the top of the stairs.

Staff are the rudest in the industry … awful customer service … will never fly Avianca again

Pros: we leave and arrive on time Cons: the most uncomfortable seats ever. You cant recline at all your seats. No entertainment No TVs flight attendants didn't provide even a glass of water. You have to go to back of the airplane and ask for one. I am Colombian and I remember seeing the flight attendants very neat, elegants which is or was a staple of Avianca.it was one with tennis shoes, no male up, the hair was messy... that was really odd.

Here we have another airline flying to Guatemala but doesn't have a plus or a less, just in the middle. Why? Well, first we don't have even free water Movie selection is poor Seats don't recline in some places Food selection is carb based Forgot to mention, customer service on the web is the worst. Good things; Very reliable on schedule Kind crew

Last seat of Bussines Class it does recline but passenger seating behind kept pushing since they did not have space once my seat was reclined

I like the crew they're very friendly. I don't like. on five hour flight they not offered snacks. Any drink. Not even coffee

Not even water is offered on the flight. You cannot lean back on the seats and the seats are so narrow you can’t avoid rubbing elbows with the person next to you.

I couldnt recline the seat. Other than that crew was very attentive and helpful. Thsnk you

I had to go to the boarding counter for them to enter my return flight as it’s not with Avianca. There was a long queue as there were lots of people being called to the counter.

Everything went well. The flight was slightly delayed however we landed on time.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

Good! But your flight crews don’t need to ‘eat the mics’ when making announcements. If they held the mics 3 to 4 inches away from their mouths, we could understand them so much better. Otherwise, all is well.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.

Horrible experience. First and last time using this airline. Made an announcement that boarding will start in 15 minutes, canceled the flight 5 minutes later due to no airline staff. Had to book another flight on Delta since Spirit had no other flights arriving to my original destination the same day. I wouldn't recommend anyone to fly with Spirit. No wonder why it consistently ranks high among worst airlines.

Once again, the staff seem to think they are above the customers and treat everyone with disdain, belittling people.

Sadly there was a crew member very rude with my kid and with me.

Everything you need to know for your flight from Chicago to Costa Rica

Information on your arrival and departure airports