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Find cheap flights from Chicago to Costa Rica from $96

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 8/22. 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 6/29
Sat 7/6

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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$258
Liberia
Liberia2 stops$583

Good to know

Low season

September

High season

March

Cheapest flight

$96
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 57% more expensive 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 2617 reviews
7.7Comfort
8.1Boarding
8.3Crew
7.3Food
7.2Entertainment
Airline reviews

The seats had plenty of leg room and the staff were very nice.

8.0 ExcellentAnonymous, May 2024LAX - PTY
Read more about Copa Airlines reviews

The seats had plenty of leg room and the staff were very nice.

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!!"

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.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

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!

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.

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Book cheap flights from Chicago to Costa Rica

Recent round-trip flight deals

8/22Thu
1 stopSpirit Airlines
6h 35mORD-SJO
8/25Sun
2 stopsSpirit Airlines
21h 08mSJO-ORD
$258
6/19Wed
1 stopSpirit Airlines
7h 24mORD-SJO
6/26Wed
1 stopSpirit Airlines
9h 21mSJO-ORD
$259
8/11Sun
1 stopAvianca
6h 45mORD-SJO
8/23Fri
1 stopAvianca
7h 55mSJO-ORD
$297
8/9Fri
1 stopAvianca
6h 45mORD-SJO
8/22Thu
2 stopsAvianca
17h 50mSJO-ORD
$389
10/13Sun
1 stopUnited Airlines
16h 00mORD-LIR
10/17Thu
1 stopUnited Airlines
17h 33mLIR-ORD
$627
10/15Tue
1 stopAmerican Airlines
7h 03mORD-LIR
10/19Sat
1 stopAmerican Airlines
10h 01mLIR-ORD
$645
10/12Sat
1 stopAmerican Airlines
17h 52mORD-LIR
10/17Thu
1 stopAmerican Airlines
16h 26mLIR-ORD
$647
10/29Tue
1 stopDelta
6h 43mMDW-LIR
11/3Sun
1 stopDelta
7h 36mLIR-MDW
$647
9/6Fri
1 stopDelta
6h 39mORD-LIR
9/12Thu
2 stopsDelta
17h 13mLIR-ORD
$651
7/18Thu
1 stopUnited Airlines
19h 53mORD-LIR
7/21Sun
nonstopUnited Airlines
5h 17mLIR-ORD
$697

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Recent one-way flight deals

8/22Thu
1 stopSpirit Airlines
14h 34mORD-SJO
$96
6/12Wed
1 stopSpirit Airlines
30h 29mORD-SJO
$111
6/14Fri
nonstopAvianca
6h 45mORD-SJO
$324
8/22Thu
1 stopDelta
6h 43mMDW-SJO
$353
6/16Sun
1 stopAvianca
6h 45mORD-SJO
$373
8/10Sat
1 stopAmerican Airlines
17h 38mORD-LIR
$376
11/11Mon
1 stopAmerican Airlines
17h 22mORD-LIR
$377
7/20Sat
2 stopsDelta
12h 13mMDW-SJO
$378
7/20Sat
nonstopUnited Airlines
5h 14mORD-SJO
$419
6/15Sat
nonstopUnited Airlines
5h 02mORD-LIR
$513

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Last minute flights from Chicago to Costa Rica

Last minute flight, train and bus deals

6/4Tue
multi-stopSpirit Airlines
27h 02mORD-SJO
6/14Fri
multi-stopSpirit Airlines
8h 39mSJO-ORD
$293
6/4Tue
multi-stop
27h 02mORD-SJO
6/12Wed
multi-stop
7h 55mSJO-ORD
$319
6/2Sun
multi-stopAvianca
7h 50mORD-SJO
6/12Wed
multi-stopAvianca
7h 55mSJO-ORD
$446
6/2Sun
multi-stopAvianca
7h 50mORD-SJO
6/9Sun
multi-stopAvianca
7h 55mSJO-ORD
$465
6/4Tue
multi-stopDelta
12h 28mMDW-SJO
6/14Fri
multi-stopDelta
7h 39mSJO-MDW
$1,084
6/4Tue
multi-stopDelta
11h 41mMDW-SJO
6/14Fri
multi-stopDelta
7h 39mSJO-MDW
$1,089
6/4Tue
multi-stopAmerican Airlines
8h 05mORD-LIR
6/12Wed
multi-stopAmerican Airlines
17h 35mLIR-ORD
$1,194
6/4Tue
multi-stopAmerican Airlines
8h 50mORD-LIR
6/12Wed
multi-stopAmerican Airlines
8h 38mLIR-ORD
$1,198
6/2Sun
nonstopUnited Airlines
5h 02mORD-LIR
6/7Fri
multi-stopUnited Airlines
10h 06mLIR-ORD
$1,312
6/2Sun
multi-stopUnited Airlines
17h 54mORD-LIR
6/7Fri
multi-stopUnited Airlines
7h 46mLIR-ORD
$1,317

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Flights to Costa Rica

Return flight deals:

Costa Rica - Chicago

Cabin classes:

$1,269
$1,489
$350