$169 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 5/21. 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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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, Aug 25 - Tue, Sep 1
Multiple Airlines Logo
4:18 pm - 12:09 pm
SJO
-
ORD
18h 51m
1 stop
Multiple Airlines Logo
1:49 pm - 11:59 pm
ORD
-
SJO
11h 10m
1 stop
$315Multiple Airlines
Tue, Aug 25 - Sat, Aug 29
Multiple Airlines Logo
4:18 pm - 12:09 pm
SJO
-
ORD
18h 51m
1 stop
Multiple Airlines Logo
2:53 am - 11:59 pm
ORD
-
SJO
22h 06m
1 stop
$325Multiple Airlines
Tue, Aug 25 - Sat, Aug 29
Multiple Airlines Logo
4:18 pm - 12:09 pm
SJO
-
ORD
18h 51m
1 stop
Multiple Airlines Logo
2:53 am - 11:59 pm
ORD
-
SJO
22h 06m
1 stop
$327Multiple Airlines
Fri, May 1 - Sat, May 9
Spirit Airlines Logo
12:38 pm - 5:11 pm
SJO
-
ORD
27h 33m
2 stops
Spirit Airlines Logo
6:32 pm - 11:33 am
ORD
-
SJO
18h 01m
2 stops
$329Spirit Airlines
Thu, Apr 30 - Sun, May 3
Spirit Airlines Logo
12:38 pm - 5:11 pm
SJO
-
ORD
27h 33m
2 stops
Spirit Airlines Logo
6:16 pm - 11:33 am
ORD
-
SJO
18h 17m
2 stops
$335Spirit Airlines
Tue, Aug 25 - Sat, Aug 29
Volaris Logo
4:18 pm - 12:09 pm
SJO
-
ORD
18h 51m
1 stop
Volaris Logo
2:53 am - 11:59 pm
ORD
-
SJO
22h 06m
1 stop
$347Volaris
Fri, May 1 - Tue, May 5
United Airlines Logo
3:27 pm - 7:54 am
LIR
-
ORD
15h 27m
1 stop
United Airlines Logo
9:56 pm - 12:10 pm
ORD
-
LIR
15h 14m
1 stop
$614United Airlines
Fri, May 1 - Tue, May 5
United Airlines Logo
1:20 pm - 12:45 am
LIR
-
ORD
10h 25m
1 stop
United Airlines Logo
8:10 pm - 12:10 pm
ORD
-
LIR
17h 00m
1 stop
$635United Airlines
Wed, Jul 15 - Tue, Jul 21
American Airlines Logo
12:35 pm - 12:24 am
LIR
-
ORD
10h 49m
1 stop
American Airlines Logo
6:00 pm - 11:22 am
ORD
-
LIR
18h 22m
1 stop
$658American Airlines
Thu, Jul 30 - Sat, Aug 29
American Airlines Logo
2:47 pm - 6:52 am
LIR
-
ORD
15h 05m
2 stops
American Airlines Logo
10:10 pm - 11:44 am
ORD
-
LIR
14h 34m
2 stops
$663American 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 flight to Chicago O'Hare Airport?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from San José, at $315 return. The most popular connection is from Boston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $138 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $411. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $563 on average.

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 January, where tickets cost $384 on average for return flights. On the other hand, the most expensive months are March and April, where the average cost of tickets from Costa Rica is $540 and $500 respectively. For one-way flights, the best month to travel is January with an average price of $384.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all round-trip flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, when round-trip flights cost $464 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $467.

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 Liberia $159 round-trip, from San José $274 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 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$169
Best time to beat the crowds with an average 15% 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 O'Hare Airport flights

  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 3 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from San José, at $315 return. The most popular connection is from Boston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $138 in the last 3 days.

  • 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 $380. The cheapest price found on KAYAK in the last 2 weeks cost $159 and departed from Liberia Airport.

  • 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.

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 Liberia $179, from San José $246
  • 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.
7.5
Copa AirlinesOverall score based on 1569 reviews
6.8Entertainment
7.8Boarding
7.4Comfort
8.1Crew
6.8Food
Airline reviews

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

2.0 MediocreEdwin, Mar 2026
LIM - PTY
Read more Copa Airlines reviews

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

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

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

I had bad experiences before now was excellent I am glad they have business class again

Horrible experience with Avianca, they delayed their flight and when we arrived to NYC, AVIANCA took 1 hr y 30 mins to park the airplane and all passenger get off the plane, it made me lost all my trains to get back home and I came back to my place at 3 am instead of 12 am. On the top of that their plane seat are so uncomfortable and is not enough space and killed my legs and knees, Avianca used to be good when it was a Colombian company, now after Brasilian company bought them, their service quality is bad and their flights are delayed and oversold.

I actually upgraded to the medium level of seats from basic and even doing that it may have been physically the most uncomfortable flight I have ever had. They packed everyone like is a train to death camp. It was a red eye so I hoped to get some sleep but it was physically impossible to find a comfortable way to rest. I met other folks on the same flight and they said the same thing. It was an utterly miserable flight and if I have any other options I will never fly with them again

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

No free snacks nor drinks on very short 30min flight. Entertainment system is over wifi to your own phone or tablet, which is good but often a show or movie just stops and refuses to continue

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

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

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Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago