$182 Find Cheap Flights from Costa Rica to Chicago - Compare and Save

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 10/1. 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.
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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

Sat, Oct 24 - Sun, Oct 25
Air Canada Logo
1:00 pm - 9:23 am
LIR
-
ORD
19h 23m
1 stop
Air Canada Logo
1:57 pm - 1:10 pm
ORD
-
LIR
24h 13m
1 stop
$377Air Canada
Thu, Oct 15 - Tue, Oct 20
Copa Airlines Logo
5:55 pm - 1:59 pm
SJO
-
ORD
19h 04m
1 stop
Copa Airlines Logo
8:01 am - 7:10 am
ORD
-
SJO
24h 09m
1 stop
$381Copa Airlines
Sat, Oct 10 - Sat, Oct 24
Copa Airlines Logo
10:03 am - 12:57 am
SJO
-
ORD
13h 54m
1 stop
Copa Airlines Logo
8:01 am - 7:04 am
ORD
-
SJO
24h 03m
1 stop
$381Copa Airlines
Sat, Oct 24 - Tue, Oct 27
Air Canada Logo
1:00 pm - 1:13 pm
LIR
-
ORD
23h 13m
1 stop
Air Canada Logo
9:05 pm - 1:10 pm
ORD
-
LIR
17h 05m
1 stop
$401Air Canada
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$422Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
9:20 am - 6:45 pm
MDW
-
SJO
10h 25m
2 stops
$438Southwest
Fri, Jan 22 - Sun, Jan 24
United Airlines Logo
2:05 pm - 7:35 pm
SJO
-
ORD
5h 30mnonstop
United Airlines Logo
7:39 am - 12:56 pm
ORD
-
SJO
5h 17mnonstop
$523United Airlines
Tue, Dec 22 - Wed, Jan 6
United Airlines Logo
1:55 pm - 7:28 pm
SJO
-
ORD
5h 33mnonstop
United Airlines Logo
7:17 am - 12:35 pm
ORD
-
SJO
5h 18mnonstop
$523United Airlines
Thu, Sep 3 - Wed, Sep 9
American Airlines Logo
2:56 pm - 12:35 am
SJO
-
ORD
8h 39m
1 stop
American Airlines Logo
9:01 pm - 11:59 am
ORD
-
SJO
15h 58m
2 stops
$531American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
2:56 pm - 7:34 am
SJO
-
ORD
15h 38m
1 stop
American Airlines Logo
6:00 am - 1:52 pm
ORD
-
SJO
8h 52m
1 stop
$538American 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 day to fly to Chicago?

The average price of all round-trip flights to Chicago 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 $369. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $524 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, 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 is January, where tickets cost $385 on average for return flights. On the other hand, the most expensive months are July and June, where the average cost of tickets from Costa Rica is $634 and $561 respectively. For one-way flights, the best month to travel is December with an average price of $258.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago 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 is generally in the morning, when round-trip flights cost $463 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $465.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From San José $491 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $144.

Good to know

Low season

April

Cheapest flight

$182
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $499. The cheapest price found on KAYAK in the last 2 weeks cost $201 and departed from San José Juan Santamaria Intl Airport.

  • 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.

  • How many direct flights to Chicago are there each week?

    Each week there are around 38,042 direct flights from within Costa Rica to Chicago. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $364 or less one-way and $491 or less round-trip.
  • 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.
8.0
SouthwestOverall score based on 4221 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

stood in line to check in luggage for nearly an hour. very poor service and not excusable

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

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

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

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

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

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

I would like a glass of wine or some kind of alcoholic drink.

Very long delay but we just made the connection. The requested wheel chairs were not there so I had to assist/carry BOTH of my parents to the gate while carrying their bags so we could make the connection. The plane had no entertainment system and NO WIFI, legroom zero. Restrooms on ALL of flights were dirty and one restroom did not even work properly. I was surprised to see COPA like this since my flight with them in 2013 was incredible, the seats were amazing and the food options were spectacular. Of course, I see this kind of service on many airlines now, with services and hospitality at an all time low. The worse part of the trip was seeing my 90 year old parents go through hell on these flights and having to try and rush to a gate to make the next flight. Never again

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

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.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Better seats, allow us to upgrade, terrible website, poor telephone service, better equipment

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 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

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

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!

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

why did we have to go through security mid flight

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
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Schererville
Porter
Monticello
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Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.