$132 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 3/31. 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$326
Liberia
Liberia2 stops$454
San José
San José2 stops$326
Liberia
Liberia2 stops$454

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

Tue, Apr 14 - Sat, Apr 25
Multiple Airlines Logo
6:31 am - 8:45 am
ORD
-
SJO
27h 14m
2 stops
Multiple Airlines Logo
7:45 am - 6:15 pm
SJO
-
ORD
9h 30m
1 stop
$326Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
10:49 am - 10:43 pm
ORD
-
SJO
11h 54m
1 stop
American Airlines Logo
7:00 am - 12:24 pm
SJO
-
ORD
5h 24mnonstop
$327American Airlines
Fri, Feb 20 - Sat, Mar 7
Multiple Airlines Logo
5:58 pm - 8:10 am
ORD
-
SJO
14h 12m
2 stops
Multiple Airlines Logo
12:35 pm - 11:38 pm
SJO
-
ORD
11h 03m
1 stop
$328Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Spirit Airlines Logo
5:15 am - 11:22 am
ORD
-
SJO
7h 07m
1 stop
Spirit Airlines Logo
12:31 pm - 11:41 pm
SJO
-
ORD
10h 10m
1 stop
$329Spirit Airlines
Tue, Apr 7 - Thu, Apr 16
Spirit Airlines Logo
5:05 am - 11:14 am
ORD
-
SJO
7h 09m
1 stop
Spirit Airlines Logo
12:31 pm - 11:41 pm
SJO
-
ORD
10h 10m
1 stop
$330Spirit Airlines
Tue, Mar 31 - Wed, Apr 8
Multiple Airlines Logo
4:51 pm - 3:05 pm
ORD
-
SJO
23h 14m
1 stop
Multiple Airlines Logo
11:38 am - 11:36 pm
SJO
-
ORD
10h 58m
1 stop
$331Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
9:18 am - 11:30 pm
ORD
-
SJO
14h 12m
3 stops
Multiple Airlines Logo
12:31 pm - 9:13 pm
SJO
-
ORD
7h 42m
1 stop
$332Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
United Airlines Logo
7:39 am - 12:56 pm
ORD
-
SJO
5h 17mnonstop
United Airlines Logo
12:35 pm - 12:26 am
SJO
-
ORD
11h 51m
1 stop
$333United Airlines
Wed, Mar 4 - Thu, Mar 19
Copa Airlines Logo
2:22 pm - 9:46 pm
ORD
-
SJO
7h 24m
1 stop
Copa Airlines Logo
11:01 am - 1:04 am
SJO
-
ORD
13h 03m
1 stop
$335Copa Airlines
Sun, Feb 22 - Fri, Feb 27
Delta Logo
7:59 pm - 12:50 pm
ORD
-
LIR
16h 51m
1 stop
Delta Logo
2:45 pm - 1:20 pm
LIR
-
ORD
22h 35m
2 stops
$495Delta
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 $358 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 $358.

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 $610 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$132
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 $502 on average. Morning departures are around 23% 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 1561 reviews
7.4Comfort
6.8Entertainment
6.8Food
7.8Boarding
8.1Crew
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.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

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.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

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.

It was delayed and I lost my connection flight to Cali and I missed my Mom's funeral

I upgraded to businesses class. Because of that the flight was comfortable.

I actually upgraded to the medium level of seats from basic and even doing that it may have been physically the most uncomfortable flight I have ever had. They packed everyone like is a train to death camp. It was a red eye so I hoped to get some sleep but it was physically impossible to find a comfortable way to rest. I met other folks on the same flight and they said the same thing. It was an utterly miserable flight and if I have any other options I will never fly with them again

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

It was smooth sailing snags we had a really smooth landing and a great flight!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

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

Information on your arrival and departure airports