ORD - SJO

$137 Find Cheap Flights from Chicago O'Hare Airport to San José

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to San José departing on 8/9. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
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Flights Deals

Cheap Flights from O'Hare Intl to San José (ORD-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to San José 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 O'Hare Intl to San José

Tue, Jul 8 - Tue, Jul 22
 Logo
10:46 am - 11:11 amORD-SJO
25h 25m2 stops
 Logo
5:05 am - 4:05 pmSJO-ORD
10h 00m1 stop
Tue, Jul 8 - Tue, Jul 22
Spirit Airlines Logo
10:46 am - 11:11 amORD-SJO
25h 25m2 stops
Spirit Airlines Logo
11:24 am - 7:50 amSJO-ORD
19h 26m2 stops
$305Spirit Airlines
Find Deal
Wed, Nov 5 - Wed, Nov 12
Copa Airlines Logo
6:56 am - 6:56 pmORD-SJO
12h 00m1 stop
Copa Airlines Logo
8:44 am - 11:21 pmSJO-ORD
14h 37m1 stop
$310Copa Airlines
Find Deal
Mon, Jun 30 - Thu, Jul 3
Copa Airlines Logo
3:07 pm - 8:20 amORD-SJO
18h 13m1 stop
Copa Airlines Logo
5:52 pm - 1:42 pmSJO-ORD
18h 50m1 stop
$325Copa Airlines
Find Deal
Sat, Jun 28 - Sat, Jul 12
Frontier Logo
5:01 am - 12:31 pmORD-SJO
8h 30m1 stop
Frontier Logo
1:47 pm - 11:29 pmSJO-ORD
8h 42m1 stop
$335Frontier
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
6:00 am - 1:29 pmORD-SJO
7h 29m1 stop
Frontier Logo
2:49 pm - 11:21 pmSJO-ORD
8h 32m1 stop
$348Frontier
Find Deal
Tue, Jul 15 - Tue, Jul 22
Avianca Logo
5:25 pm - 7:40 amORD-SJO
15h 15m2 stops
Avianca Logo
5:05 am - 4:05 pmSJO-ORD
10h 00m1 stop
$368Avianca
Find Deal
Wed, Sep 3 - Mon, Sep 8
American Airlines Logo
9:51 am - 7:42 pmORD-SJO
10h 51m2 stops
American Airlines Logo
12:12 pm - 11:48 pmSJO-ORD
10h 36m2 stops
$386American Airlines
Find Deal
Thu, Aug 28 - Thu, Sep 4
American Airlines Logo
10:25 am - 6:15 pmORD-SJO
8h 50m1 stop
American Airlines Logo
12:12 pm - 11:39 pmSJO-ORD
10h 27m2 stops
$413American Airlines
Find Deal
Fri, Jul 11 - Tue, Aug 12
Avianca Logo
3:45 pm - 11:35 pmORD-SJO
8h 50m2 stops
Avianca Logo
5:05 am - 4:05 pmSJO-ORD
10h 00m1 stop
$419Avianca
Find Deal
Expert advice

Expert advice for your flight from O'Hare Intl to San José

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
ORD

Security lines at ORD can exceed 30 minutes during peak times. Arrive early to avoid delays, especially for international flights.

Read more about ORDby Stefanie Waldek
SJO

For a smooth arrival at SJO, pre-arrange ground transportation through your hotel to avoid long waits and ensure a hassle-free transfer.

Read more about SJOby Mark Chesnut
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Chesnut

Mark Chesnut

Expert on SJO

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more
Useful Info

KAYAK's insights & trends for O'Hare Intl to San José flights

Get data-powered insights and trends into flights from O'Hare Intl to San José to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to San José?

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

If your flying dates are flexible, you should consider flying to San José on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago O'Hare Airport to San José. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, 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 from Chicago O'Hare Intl Airport to San José is August, where tickets cost $432 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $769 and $698 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to San José?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $526 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, 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 on the flight from Chicago O'Hare Intl Airport to San José, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$137
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport to San José

When to book flights from O'Hare Intl to San José

Are your dates flexible? Find out the best times to travel from O'Hare Intl to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to San José flights

  • What is the luggage allowance on Aeromexico flights from Chicago O'Hare Airport to San José?

    For flights from Chicago O'Hare Airport to San José with Aeromexico, the maximum weight allowance is 55 pounds for all regular and Premiere fares and the maximum linear dimension limit is 62 inches. Passengers may bring one carry-on bag of up to 22 lbs plus one personal item. Fees apply for oversize and overweight luggage and will depend on the fare type and flight route.

  • How do I get from San Jose Airport (SJO) to the city center?

    The bus is the most affordable way to get to the city center. The bus stop is located just outside the airport terminal. Take the Alajuela-San Jose bus and get off at the last stop, which is in the center of San Jose. The trip takes around 45 minutes. Taxis are also available at the airport and can bring you directly to your destination in the city center.

  • What seat selection options are available on Avianca flights from Chicago O'Hare Airport to San José?

    Avianca offers various seat selection options on flights from Chicago O'Hare Airport to San José. Passengers can choose seats from the available standard seating options at no additional cost during the check-in process. Avianca also offers preferred seats for an additional fee. These seats are typically located in the front rows of the cabin or have extra legroom.

  • What services are offered by Copa Airlines to economy class passengers on flights from Chicago O'Hare Airport to San Jose?

    Copa Airlines offers a variety of services to economy class passengers on its flights from Chicago O'Hare Airport to San José. Economy class passengers can enjoy Copa Airlines' in-flight entertainment system, which includes movies, TV shows, and music. Passengers in economy class also receive complimentary meals and drinks on all Copa Airlines flights.

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San José?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San José was $137 for a one-way ticket and $289 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and San José?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago O'Hare Airport and on arrival in San José.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to San José?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to San José flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to San José?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to San José flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to San José?

    Star Alliance is the only airline alliance operating flights between Chicago O'Hare Airport and San José.

  • On which days can I fly direct from Chicago O'Hare Airport to San José?

    You can catch a nonstop flight from Chicago O'Hare Airport to San José on Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to San José, Copa Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San José are Copa Airlines and United Airlines. With an average price for the route of $608 and an overall rating of 7.5, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $754 and an overall rating of 7.4.

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

    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 O'Hare Airport to San José.

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

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

    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 San José with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and SJO can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to San José?

    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 San José from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to San José

  • Looking for a cheap flight? 25% of our users found flights on this route for $202 or less one-way and $507 or less round-trip.
  • US citizens require a valid visa to enter Costa Rica, including for flights from Chicago O'Hare International Airport (ORD) to San José (SJO). The type of visa needed depends on the purpose of travel, and there are several options such as tourist visas, work visas, and student visas.
  • Spirit Airlines assists passengers who require a wheelchair to get to and from their gate or assistance in boarding and disembarking the aircraft. The airline also offers special seating options for passengers with reduced mobility on flights from Chicago O'Hare Airport to San José, including seats with movable armrests and bulkhead seats.
  • Air Canada allows pets to travel in the cabin or as checked baggage on flights from Chicago O'Hare Airport to San José. For pets traveling in the cabin, only dogs and cats are permitted and the pet carrier will count as one of the traveler's carry-on items. For pets traveling as checked baggage, Air Canada only accepts cats and dogs, and they must be at least 12 weeks old.
  • JetBlue offers early boarding for families with children under the age of 2 and one accompanying adult on flights from Chicago O'Hare Airport to San José. This allows families to get settled on the plane before other passengers.
  • Frontier Airlines operates flights from Chicago O'Hare Airport to San José with fuel-efficient aircraft equipped with advanced technology and optimized performance capabilities to reduce carbon emissions.

Prefer to fly direct from Chicago O'Hare Airport to San José?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to San José Juan Santamaria Intl.
Find which airlines fly direct from Chicago O'Hare Intl Airport to San José Juan Santamaria Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

San José Juan Santamaria Intl to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 5 airlines serving from O'Hare Intl to San José

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to San José? 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 1453 reviews
6.8Food
7.7Boarding
7.4Comfort
8.1Crew
6.8Entertainment
Airline reviews

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

2.0 MediocrePaul, May 2025MIA - PTY
Read more Copa Airlines reviews

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

The flight was delayed twice and I could not speak with anyone at the airport about checking in. The phone number to Copa - the customer service agents were polite. They are just limited at helping because they are not at the airport

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

No headphones given for inflight entertainment. I missed my flight from the previous day and the customer service agent tried to extort an additional $100.00 US from me for missing my flight. Really?!

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

It was good, plane is a bit older so seats are somewhat flat

Great from check in all the way to the end. Very happy with Copa

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

I loved my experience. Very safe, Very informative and very friendly.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Seats are very tight even in Plus, no complimentary snacks or beverage

Late departure. When the flight arrived in Medellin the plane sat at the gate for 20 minutes waiting for a bus for us to get off the plane.

I receive a service for what I pay, so it is fair.

A few years ago long flights 6 hours or so used to have video screens and they offered ear phones. The food cart used to come and drinks. Now absolutely nothing. Avianca is as bad as Spirit Airlines. Avianca will now be my last choice when booking my next flight.

Terrible, We had to stay in Bogota for two days due to weather but the airline did not provide for the same day flight. Only two days later

There isn't much space in-between seats and even water needs to be paid for during the flight.

We did not know about the bag fees until check in. They are way too high. It’s insane. We also had a huge delay and everything costed extra which was very annoying.

Boarding was somewhat confusing in that the wrong messages were being displayed at the gate. It was somewhat annoying that I got off one flight and straight onto another (from the same gate), but in between they re-checked my hand luggage and made me get rid of my water (which they charge for on the plane). I was sitting in their 'Plus' seating, but the leg room was still too small to be able to sit square. The food options on the flights are pretty cheap quality (but not price). They got me from 'A' to 'B' on-time and for a relatively good price, but the experience itself was below average.

Lounge for business was closed. Boarding was rush and stand by. Seat for business is just the middle seat blocked and some more leg room.

Flew with our two children. Paid $380 to check two bags (one was overweight). They then left the bags behind on Sunday, December 21st, with all our family’s clothes and family Christmas presents. When we arrived at our destination they told us the bags had not arrived, and they thought (but didn’t know) they were still in Boston, but that there’d be a flight the next day and the bags would arrive the next day. The next day we found out there was no flight, now we’re hoping we get our bags before we fly back out. Meanwhile, trying to get any engagement or accurate information is a waste of time. The folks at the call center are just gatekeepers, who can’t connect with any departments that actually do things to solve a problem. Getting information is made deliberately difficult. My biggest regret is that I’ve had a number of awful experiences with Avianca traveling between the US and Colombia, and still let myself get suckered into buying these tickets because the schedule was great. Never again.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

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