$130 Find Cheap Flights from Costa Rica to Chicago O'Hare Airport

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 3/7. 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.
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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$307
Overall average: $474
Multiple Airlines
Tue 4/14Mon 4/27
SJO - ORD • 1 stop
Cheapest non-stop
$318
Typical prices: $346-$574
American Airlines
Sat 2/14Wed 2/18
SJO - ORD • Non-stop
Top airlines
American Airlines
Most flights • 23 per week
Copa Airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 13% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
Flight Deals

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

Tue, Apr 14 - Mon, Apr 27
Multiple Airlines Logo
11:38 am - 7:59 am
SJO
-
ORD
19h 21m
1 stop
Multiple Airlines Logo
6:31 am - 8:45 am
ORD
-
SJO
27h 14m
2 stops
$307Multiple Airlines
Thu, Feb 12 - Tue, Feb 24
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m
2 stops
Spirit Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m
2 stops
$310Spirit Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
12:35 pm - 12:26 am
SJO
-
ORD
11h 51m
1 stop
United Airlines Logo
7:39 am - 12:56 pm
ORD
-
SJO
5h 17mnonstop
$312United Airlines
Fri, Feb 20 - Mon, Feb 23
Spirit Airlines Logo
1:31 pm - 11:47 pm
SJO
-
ORD
10h 16m
1 stop
Spirit Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m
2 stops
$313Spirit Airlines
Sat, Feb 21 - Tue, Feb 24
Multiple Airlines Logo
8:07 am - 7:54 am
SJO
-
ORD
23h 47m
2 stops
Multiple Airlines Logo
12:44 pm - 12:22 pm
ORD
-
SJO
23h 38m
3 stops
$314Multiple Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
7:00 am - 12:24 pm
SJO
-
ORD
5h 24mnonstop
American Airlines Logo
3:10 pm - 8:12 pm
ORD
-
SJO
5h 02mnonstop
$318American Airlines
Mon, Mar 2 - Mon, Mar 9
Copa Airlines Logo
6:08 pm - 12:31 pm
SJO
-
ORD
18h 23m
1 stop
Copa Airlines Logo
3:22 pm - 8:20 am
ORD
-
SJO
17h 58m
1 stop
$320Copa Airlines
Mon, Apr 6 - Fri, Apr 10
Air Canada Logo
2:55 pm - 5:45 pm
LIR
-
ORD
25h 50m
1 stop
Air Canada Logo
12:50 pm - 2:30 pm
ORD
-
LIR
26h 40m
1 stop
$510Air Canada
Mon, Feb 23 - Fri, Feb 27
United Airlines Logo
8:35 am - 11:16 am
LIR
-
ORD
26h 41m
1 stop
United Airlines Logo
7:49 am - 12:55 pm
ORD
-
LIR
5h 06mnonstop
$548United Airlines
Mon, Apr 6 - Fri, Apr 10
American Airlines Logo
1:32 pm - 8:00 pm
LIR
-
ORD
5h 28mnonstop
American Airlines Logo
5:00 am - 11:28 am
ORD
-
LIR
7h 28m
1 stop
$1,074American Airlines
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 February, where tickets cost $389 on average for one-way flights. On the other hand, the most expensive months are June and April, where the average cost of tickets from Costa Rica is $505 and $474 respectively. For return trips, the best month to travel is February with an average price of $389.

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 $172 one-way - $302 round-trip, from Liberia $223 one-way - $452 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 63 days before departure.

Good to know

Low seasonFebruary
Cheapest flight$130
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport 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 $358. The cheapest price found on KAYAK in the last 2 weeks cost $141 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 Thursday where tickets can be as cheap as $418. On the other hand, the most expensive day to fly is Sunday, where prices are $575 on average.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

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

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 morning, when flights cost $463 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 $466.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From San José $237, from Liberia $338
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport 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
6.8Food
6.8Entertainment
7.4Comfort
8.1Crew
7.8Boarding
Airline reviews

Seats were awful. Media should have been included for such a long flight.

4.0 OkayPaul, Jan 2026
LIM - PTY
Read more Copa Airlines reviews

Seats were awful. Media should have been included for such a long flight.

A lot things happened in this trip.The fly should be less stress.

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

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.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

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

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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.

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

I handed in my suitcase in perfect condition at SAL Airport. And in MIA Airport I received it with one corner broken and the wheels bent.

I like the crew members they're very friendly. Clean plane. The flight was on time. I dont like the comfort my car seat its better that the plane seats. They charge for everything. This airline was very good. Now it's a low cost airline

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

I had to go to the boarding counter for them to enter my return flight as it’s not with Avianca. There was a long queue as there were lots of people being called to the counter.

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

The usb plugs for charging your phone didn’t work, the seats were coarse and hard. Not very comfortable. No inflight WiFi

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 seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

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