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Find cheap flights from Chicago to Costa Rica from $108

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 6/5. 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
0 bags
Sat 6/15
Sat 6/22

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Best Costa Rica Flight Deals

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

San José
San José1 stop$256
Liberia
Liberia1 stop$647

Good to know

Low season

September

High season

March

Cheapest flight

$108
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago O'Hare Airport to San José

FAQs - booking Costa Rica flights

  • How many airlines fly from Chicago to Costa Rica?

    Many airlines travel this particular route, including America, Major, United, Interjet, Spirit, Alaska, and Frontier, among others. United takes the win when it comes to their non-stop trips, but American and Major rank among the most preferred due to the quality of service they are known to offer.

  • How can I get from the city center to Chicago O'Hare Intl?

    If you're coming from downtown Chicago towards Chicago O'Hare Intl, there is a train, a number of coaches, airport shuttles, and cabs available. If you are using your car, there are parking spaces in the Main Garage. The economy lots are ideal for extended parking and for saving money.

  • Which airport in Costa Rica allows domestic flights to other cities in the country?

    San José Juan Santamaria Intl is known to offer international flights and domestic flights as well. This means that you can easily use the airport to fly to other cities within the country. Liberia also allows domestic flights to other parts of Costa Rica, such as Samara and Tamarindo.

  • What are the car seat laws every traveler should know about while in Costa Rica?

    If you are traveling with a child, you'll need a car seat. Children under 12 years old and shorter than 57 inches need to be strapped into a car seat or a booster.

  • 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 to Costa Rica from Chicago 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 to Costa Rica with an airline and back to Chicago 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 to Costa Rica from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Costa Rica

  • Morning departure is around 26% cheaper than an evening flight, on average*.
  • Traveling from Chicago to Costa Rica usually means using either Chicago O'Hare Intl or Chicago Midway. The former airport offers numerous domestic and international direct trips.
  • Chicago O'Hare Intl is home to four terminals that are brimming with dining options, shops, and high-quality lounges. Spas and yoga rooms are available as well.
  • Chicago Midway focuses primarily on domestic flights, with a few exceptions, of course. It's much smaller and less crowded, which makes it easy to maneuver.
  • Chicago Midway boasts a good number of shops and restaurants but doesn't have lounges. The shops and restaurants are located in concourse A through C.
  • Airlines, such as Delta and Southwest, are known to fly to and from Chicago Midway, while over 70 airlines operate from Chicago O'Hare.
  • Travelers coming from Chicago can either land at San José Juan Santamaria Intl or Liberia Intl. The former is near top nature destinations and attractions.
  • San José Juan Santamaria Intl is home to many restaurants, cafés, fast food eateries, and shops. Massage parlors are available to help you wind down.
  • To access top surfing destinations, fly into San José Juan Santamaria Intl, which allows you to access the central and southern coasts.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.8
Copa AirlinesOverall score based on 2707 reviews
8.1Boarding
8.3Crew
7.2Entertainment
7.3Food
7.7Comfort
Airline reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

8.0 ExcellentAntonio, Mar 2024LAX - PTY
Read more about Copa Airlines reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"
Pros: "Copa was convenient and easy. Very easy boarding process and I appreciated the day flight."
Cons: "This is a business class that is equivalent to a US carrier domestic first class. Good seats, not lay flat but wide on my 737-800. The food and service emulated say American Airlines Domestic 1C as well. Everything was just good enough, and much cheaper that international business on the majors."

No water for a 5 hour flight entertainment not working seats with little room for knees when person in front of me reclined kept bumping my knees.

I don't think anyone actually reads these comments, so I won't spend much time on this submission. If you want to talk, you know how to reach me. The D/FW manager of Avianca (self-identified), Juan Calderon, insisted I buy an onward ticket from San Salvador even though I have diplomatic status in El Salvador and live here. It cost me $1,393 and Mr Calderon would not let me make the ticked flexible so I could get a refund. He went out of his way to be rude to me. He gave me seat 32K -- windowless window seat in the last row and did not offer to let me upgrade even though there were plenty of seats. I have flown well over a million miles in my life and this is the worst experience I have ever had. I would like a refund on the ticket I was forced to buy. Just awful!

This is the Spirit of Latino travel. And don’t even get me started on customer service.

Awful. I checked in online and there was no option to pay for baggage, at the airport when I checked in my baggage was received and Iwas not charged. When I got to LA during the boarding process I was told I didn't pay for baggage, the crew resolved I was let in the plane. When I got to my final destination my baggage was not there. It took me two days to receive my baggage. Bad service ever!

There was no food or drink service, couldn’t even get a glass of water for free. It was a long and expensive flight to not offer food or beverage on the plane.

It is better at the jfk than my home country. It was very easy and everything was on time.

There is no food. There is no in-inflight entertainment. The seats are cardboard. The airline is a living hellscape.

My experience was amazing! They helped my elderly mother board on early through a wheelchair and were accommodating to have us sit together since our seats were in different locations. When landing at the airport in GUA they were very helpful with full of hospitality.

No complimentary snacks food, beverage (not even water), pillow and blanket on a 6 hours long flight (including economy comfort). A low form of nickeling an diming. Lost a recurring passanger over a soda. Avianca never again.

Flight departure late. Got late in Colombia making us take a different flight next day. Avianca airport crew messed up my ticket so when a I got in Brazil I didn’t have a ticket for my destination. Had to buy a new ticket out of my pocket.

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Book cheap flights from Chicago to Costa Rica

Recent round-trip flight deals

6/5Wed
1 stopSpirit Airlines
7h 24mORD-SJO
6/11Tue
1 stopSpirit Airlines
8h 02mSJO-ORD
$256
5/29Wed
2 stopsSpirit Airlines
17h 44mORD-SJO
6/3Mon
1 stopSpirit Airlines
8h 38mSJO-ORD
$257
6/5Wed
nonstopAvianca
6h 45mORD-SJO
6/12Wed
1 stopAvianca
7h 30mSJO-ORD
$356
8/7Wed
1 stopAvianca
6h 45mORD-SJO
8/13Tue
1 stopAvianca
21h 15mSJO-ORD
$370
8/7Wed
1 stopDelta
6h 53mMDW-SJO
8/14Wed
1 stopDelta
7h 34mSJO-MDW
$646
9/7Sat
1 stopAmerican Airlines
17h 52mORD-LIR
9/11Wed
1 stopAmerican Airlines
17h 50mLIR-ORD
$647
9/7Sat
2 stopsAmerican Airlines
15h 51mORD-LIR
9/11Wed
2 stopsAmerican Airlines
9h 38mLIR-ORD
$648
8/11Sun
1 stopDelta
6h 43mORD-LIR
8/16Fri
1 stopDelta
9h 46mLIR-ORD
$667
10/6Sun
1 stopUnited Airlines
17h 00mORD-LIR
10/12Sat
1 stopUnited Airlines
11h 08mLIR-ORD
$757
7/5Fri
1 stopUnited Airlines
18h 10mORD-LIR
7/12Fri
1 stopUnited Airlines
16h 48mLIR-ORD
$769

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Recent one-way flight deals

6/5Wed
2 stopsSpirit Airlines
14h 08mORD-SJO
$108
6/1Sat
1 stopSpirit Airlines
18h 50mORD-SJO
$116
6/5Wed
nonstopAvianca
6h 45mORD-SJO
$182
6/2Sun
nonstopAvianca
6h 45mORD-SJO
$187
11/12Tue
1 stopDelta
6h 43mORD-LIR
$298
7/15Mon
1 stopAmerican Airlines
9h 07mORD-LIR
$376
7/15Mon
2 stopsDelta
18h 54mMDW-LIR
$378
8/10Sat
nonstopUnited Airlines
5h 14mORD-SJO
$419
7/14Sun
1 stopUnited Airlines
18h 09mORD-LIR
$423
6/5Wed
1 stopAmerican Airlines
17h 41mORD-LIR
$436

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Last minute flights from Chicago to Costa Rica

Last minute flight, train and bus deals

5/21Tue
multi-stopSpirit Airlines
16h 45mORD-SJO
5/25Sat
multi-stopSpirit Airlines
13h 56mSJO-ORD
$388
5/21Tue
multi-stopSpirit Airlines
18h 56mORD-SJO
5/25Sat
multi-stopSpirit Airlines
13h 56mSJO-ORD
$392
5/20Mon
multi-stopDelta
12h 28mMDW-SJO
6/17Mon
multi-stopDelta
13h 46mSJO-MDW
$1,094
5/21Tue
multi-stopAmerican Airlines
8h 05mORD-LIR
6/3Mon
multi-stopAmerican Airlines
17h 46mLIR-ORD
$1,214
5/21Tue
multi-stopAmerican Airlines
8h 50mORD-LIR
6/3Mon
multi-stopAmerican Airlines
18h 51mLIR-ORD
$1,218
5/21Tue
multi-stopAeromexico
22h 58mORD-SJO
5/29Wed
multi-stopAeromexico
9h 42mSJO-ORD
$1,222
5/21Tue
multi-stopDelta
6h 57mMDW-LIR
5/24Fri
multi-stopDelta
7h 38mLIR-MDW
$1,267
5/21Tue
multi-stopUnited Airlines
17h 51mORD-SJO
5/25Sat
nonstopUnited Airlines
5h 28mSJO-ORD
$1,290
5/18Sat
nonstopUnited Airlines
5h 14mORD-SJO
5/21Tue
multi-stopUnited Airlines
14h 08mSJO-ORD
$1,296
5/19Sun
multi-stopAeromexico
22h 58mORD-SJO
5/27Mon
multi-stopAeromexico
45h 59mSJO-ORD
$1,349

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Flights to Costa Rica

Return flight deals:

Costa Rica - Chicago

Cabin classes:

$1,269
$1,489
$375