$106 Find Cheap Flights from Costa Rica to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 11/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap Flights from Costa Rica to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Costa Rica to Chicago 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 Costa Rica to Chicago

Wed, Nov 12 - Sat, Nov 15
Spirit Airlines Logo
12:34 pm - 11:06 pmSJO-ORD
10h 32m1 stop
Spirit Airlines Logo
3:26 pm - 11:39 amORD-SJO
20h 13m2 stops
$217Spirit Airlines
Find Deal
Wed, Nov 12 - Sat, Nov 15
Spirit Airlines Logo
12:34 pm - 11:06 pmSJO-ORD
10h 32m1 stop
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$230Spirit Airlines
Find Deal
Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
7:22 am - 5:04 pmSJO-ORD
9h 42m1 stop
Multiple Airlines Logo
6:05 am - 3:20 pmORD-SJO
9h 15m1 stop
$251Multiple Airlines
Find Deal
Wed, Nov 19 - Sun, Nov 23
Multiple Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
Multiple Airlines Logo
11:48 am - 12:15 pmORD-SJO
24h 27m1 stop
$259Multiple Airlines
Find Deal
Fri, Jan 23 - Tue, Jan 27
Avianca Logo
5:45 am - 1:15 pmSJO-ORD
7h 30m1 stop
Avianca Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$293Avianca
Find Deal
Tue, Dec 9 - Thu, Jan 8
Avianca Logo
5:00 am - 2:50 pmSJO-ORD
9h 50m1 stop
Avianca Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$294Avianca
Find Deal
Sat, Nov 22 - Thu, Dec 11
United Airlines Logo
2:01 pm - 7:20 pmLIR-ORD
5h 19mnonstop
United Airlines Logo
10:35 am - 6:37 pmORD-LIR
8h 02m1 stop
$457United Airlines
Find Deal
Fri, Dec 26 - Wed, Dec 31
American Airlines Logo
2:37 pm - 8:02 pmLIR-ORD
5h 25mnonstop
American Airlines Logo
8:15 am - 1:37 pmORD-LIR
5h 22mnonstop
$534American Airlines
Find Deal
Fri, Dec 26 - Wed, Dec 31
American Airlines Logo
2:37 pm - 8:02 pmLIR-ORD
5h 25mnonstop
American Airlines Logo
6:52 pm - 12:26 pmORD-LIR
17h 34m1 stop
$538American Airlines
Find Deal
Wed, Dec 17 - Sun, Dec 28
United Airlines Logo
8:35 am - 10:56 pmLIR-ORD
14h 21m1 stop
United Airlines Logo
9:23 pm - 6:37 pmORD-LIR
21h 14m1 stop
$540United Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Most flights • 8 per week
Copa Airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 12% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$217
Overall average: $408
Spirit Airlines
Wed 11/12Sat 11/15
SJO - ORD • 1 stop
Cheapest non-stop
$323
Typical prices: $394-$627
American Airlines
Sat 11/22Fri 12/5
SJO - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, 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 to Chicago O'Hare Intl Airport is September, where tickets cost $407 on average for one-way flights. On the other hand, the most expensive months are April and June, where the average cost of tickets from Costa Rica is $514 and $508 respectively. For return trips, the best month to travel is September with an average price of $407.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From San José $163 one-way - $325 round-trip.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago O'Hare Intl Airport, 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, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 90 days before departure.

Good to know

Low seasonFebruary
Cheapest flight$106
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The distance between Chicago O'Hare Intl Airport and downtown Chicago is 16 miles.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $395. The cheapest price found on KAYAK in the last 2 weeks cost $145 and departed from San José Juan Santamaria Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Monday where tickets can be as cheap as $468. On the other hand, the most expensive day to fly is Sunday, where prices are $617 on average.

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

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago 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 to Chicago?

    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 Chicago 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 Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, when flights cost $371 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $541.

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From San José $250, from Liberia $415
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

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

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Costa Rica to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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
6.9Food
7.4Comfort
7.8Boarding
8.1Crew
6.8Entertainment
Airline reviews

Some of the Air hostesses are not that friendly. Need improvement

8.0 ExcellentAnonymous, Oct 2025PTY - IAD
Read more Copa Airlines reviews

Some of the Air hostesses are not that friendly. Need improvement

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.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

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.

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

6 hour flight and have to pay for everything 100 dollars to add a carry-on bag is insane

Horrible experience. Flight cancelled. Arrived at destination 12 hs later. No one gave us an answer or any information. Very very poor service. We won’t ever travel again with Avianca

Did not fly with Pakistan International Airlines. Have never flown with Pakistan International Airlines.

The seats were uncomfortable and barely reclined at all. Very little leg room despite being business class. The crew was friendly and the food was good. Had to use my own phone for in-flight entertainment.

Very uncomfortable planes , poor service on the plane , take your own water so you don’t dehydrate , in a 6 hs flight they sold one time food and beverage . 1 plane was delayed 6 hs , I lost a connecting flight . Then in the way back they announce a delay of 2 hs so I had to take a different flight to arrive on time for my connecting flight . Avoid this airline .

The check in is the only positive thing in Avianca. The seat is the most uncomfortable I have traveled, the distance is minimal.

Not what it used to be. The sale of food makes them look greedy!

No food, terms when selling are not clear. To pricy for the service in general

Avianca is not what it used to be. So disappointing

It was horrible. My experience with Avianca. I didn’t know it was Pakistan international Airlines but anyway, whatever it is it is bad horrible you guys need to upgrade everything in those planes. And you guys charge $130 for a carry-on did they wanna let me in with my carry-on that I travel everywhere with the luggage you guys are such a dog thank you

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

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