$128 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 10/7. 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.
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Best Costa Rica Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

San José
San José1 stop$249
Liberia
Liberia1 stop$425
San José
San José1 stop$249
Liberia
Liberia1 stop$425

Cheap Flight Deals from Chicago to Costa Rica (ORD-CR0)

 
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.

Recent round-trip flight deals from Chicago to Costa Rica

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Costa Rica.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
4:35 pm - 10:27 amORD-SJO
18h 52m1 stop
Spirit Airlines Logo
11:32 am - 11:29 pmSJO-ORD
10h 57m1 stop
$249Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Spirit Airlines Logo
4:35 pm - 10:27 amORD-SJO
18h 52m1 stop
Spirit Airlines Logo
12:28 pm - 11:29 pmSJO-ORD
10h 01m2 stops
$262Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Avianca Logo
3:45 pm - 11:35 pmORD-SJO
8h 50m2 stops
Avianca Logo
8:00 pm - 2:25 pmSJO-ORD
17h 25m2 stops
$317Avianca
Find Deal
Sun, Jul 27 - Sat, Aug 2
Avianca Logo
3:45 pm - 9:20 amORD-SJO
18h 35m1 stop
Avianca Logo
8:00 pm - 2:25 pmSJO-ORD
17h 25m2 stops
$346Avianca
Find Deal
Wed, Jun 18 - Thu, Jun 26
Copa Airlines Logo
3:07 pm - 8:20 amORD-SJO
18h 13m1 stop
Copa Airlines Logo
5:52 am - 12:20 amSJO-ORD
17h 28m1 stop
$374Copa Airlines
Find Deal
Thu, Jul 17 - Thu, Jul 24
Copa Airlines Logo
7:54 am - 6:48 pmORD-SJO
11h 54m1 stop
Copa Airlines Logo
10:57 am - 11:52 pmSJO-ORD
11h 55m1 stop
$424Copa Airlines
Find Deal
Fri, Jun 27 - Sun, Jul 6
American Airlines Logo
10:05 pm - 11:15 amORD-LIR
14h 10m2 stops
American Airlines Logo
2:05 pm - 7:30 amLIR-ORD
16h 25m1 stop
$429American Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
American Airlines Logo
8:45 pm - 11:15 amORD-LIR
15h 30m2 stops
American Airlines Logo
2:05 pm - 8:51 amLIR-ORD
17h 46m1 stop
$449American Airlines
Find Deal
Thu, Sep 18 - Tue, Sep 23
United Airlines Logo
7:10 am - 2:23 pmORD-LIR
8h 13m1 stop
United Airlines Logo
3:25 pm - 12:21 amLIR-ORD
7h 56m1 stop
$465United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
7:45 am - 11:46 amORD-LIR
5h 01mnonstop
United Airlines Logo
1:03 pm - 7:28 pmLIR-ORD
5h 25mnonstop
$540United Airlines
Find Deal
Sat, May 31 - Sat, Jun 7
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Costa Rica.

The cheapest ticket to Costa Rica from Chicago O'Hare Intl Airport found in the last 72 hours was to San José, at $469 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 $469.

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.

No, with an average price for the route of $1,177, prices are generally cheapest when you fly direct.

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 August, when tickets cost $422 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $772 and $698 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 Wednesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Costa Rica, Wednesday 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. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$128
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% 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 at night, when round-trip flights cost $436 on average. Morning departures are around 75% 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 $852.

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.

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.
7.5
Copa AirlinesOverall score based on 1415 reviews
6.8Food
7.4Comfort
8.1Crew
7.8Boarding
6.8Entertainment
Airline reviews

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

4.0 OkayAnonymous, Apr 2025LAX - PTY
Read more Copa Airlines reviews

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

No headphones given for inflight entertainment. I missed my flight from the previous day and the customer service agent tried to extort an additional $100.00 US from me for missing my flight. Really?!

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

It was good, plane is a bit older so seats are somewhat flat

Great from check in all the way to the end. Very happy with Copa

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

At JFK the Security line was extremely long and few checkpoints open.

Check in person said there would be lunch. We were first class passengers and lunch was chips.

Horrible food. No wine or any other alcohol is served on the flight. Water is not served often and they refused when I asked for water in two cups. On the other hand, both going and coming back flights were on time.

Seats are getting smaller and smaller...and as hard as a rock , mediocre entertainment

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Late departure. When the flight arrived in Medellin the plane sat at the gate for 20 minutes waiting for a bus for us to get off the plane.

I receive a service for what I pay, so it is fair.

There isn't much space in-between seats and even water needs to be paid for during the flight.

We did not know about the bag fees until check in. They are way too high. It’s insane. We also had a huge delay and everything costed extra which was very annoying.

Lounge for business was closed. Boarding was rush and stand by. Seat for business is just the middle seat blocked and some more leg room.

Flew with our two children. Paid $380 to check two bags (one was overweight). They then left the bags behind on Sunday, December 21st, with all our family’s clothes and family Christmas presents. When we arrived at our destination they told us the bags had not arrived, and they thought (but didn’t know) they were still in Boston, but that there’d be a flight the next day and the bags would arrive the next day. The next day we found out there was no flight, now we’re hoping we get our bags before we fly back out. Meanwhile, trying to get any engagement or accurate information is a waste of time. The folks at the call center are just gatekeepers, who can’t connect with any departments that actually do things to solve a problem. Getting information is made deliberately difficult. My biggest regret is that I’ve had a number of awful experiences with Avianca traveling between the US and Colombia, and still let myself get suckered into buying these tickets because the schedule was great. Never again.

We were not aware carry-on bags cost extra until we arrived at the airport so, we were charged $240.00 for two small carry- on bags! There was a substantial fee for drinks and snacks. No wifi, or other entertainment was available. Waiting areas were crowded and uncomfortable.

I enjoyed it! In that case, I should have been offered this choice. On my first trip to Miami, I was asked to pay $320 for my luggage just for getting it totally broken. I cannot accept this situation at all!!!!

They charged me $120 to check one bag and then charged me another $120 for a carryon. Ridiculous!

Boarding, crew and food. Seats are too small Love Avianca

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

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