SJO - ORD

$182 Find Cheap Flights from San José to Chicago O'Hare Airport - 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 from San José to O'Hare Intl 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$381
Typical prices: $373-$606
Copa Airlines
Thu 10/15Tue 10/20
SJO - ORD • 1 stop
Cheapest non-stop
$523
United Airlines
Fri 1/22Sun 1/24
SJO - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom than standard economy.
American Main Cabin Extra includes early boarding and complimentary drinks.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 0
Direct flights
Direct flights
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Direct flights
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Top airlines
Cheapest • from $381 (round-trip)
Best reviews • 7.6 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Top layover airports
Cheapest • Avg $431 (round-trip)
Shortest trip • 7h 20m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 95% on-time
Best time • Fewest delays
Insights
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When to travel
Cheapest • 21% price drop
Most popular
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We hope you love your trip to O'Hare Intl!
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Flight Deals

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

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

Thu, Oct 15 - Tue, Oct 20
Copa Airlines Logo
5:55 pm - 1:59 pm-
19h 04m
Copa Airlines Logo
8:01 am - 7:10 am-
24h 09m
$381Copa Airlines
Sat, Oct 10 - Sat, Oct 24
Copa Airlines Logo
10:03 am - 12:57 am-
13h 54m
Copa Airlines Logo
8:01 am - 7:04 am-
24h 03m
$381Copa Airlines
Tue, Aug 25 - Sun, Aug 30
Multiple Airlines Logo
4:15 pm - 12:09 pm-
18h 54m
Multiple Airlines Logo
6:21 am - 11:59 pm-
18h 38m
$440Multiple Airlines
Fri, Oct 23 - Thu, Oct 29
JetBlue Logo
2:05 pm - 11:44 pm-
8h 39m
JetBlue Logo
7:00 am - 12:59 pm-
6h 59m
$444JetBlue
Fri, Jan 22 - Sun, Jan 24
United Airlines Logo
2:05 pm - 7:35 pm-
5h 30mnonstop
United Airlines Logo
7:39 am - 12:56 pm-
5h 17mnonstop
$523United Airlines
Tue, Dec 22 - Wed, Jan 6
United Airlines Logo
1:55 pm - 7:28 pm-
5h 33mnonstop
United Airlines Logo
7:17 am - 12:35 pm-
5h 18mnonstop
$523United Airlines
Thu, Sep 3 - Wed, Sep 9
American Airlines Logo
2:56 pm - 12:35 am-
8h 39m
American Airlines Logo
9:01 pm - 11:59 am-
15h 58m
$531American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
2:56 pm - 7:34 am-
15h 38m
American Airlines Logo
6:00 am - 1:52 pm-
8h 52m
$538American Airlines
Sun, Aug 30 - Mon, Sep 7
Avianca Logo
1:40 am - 9:20 pm-
18h 40m
Avianca Logo
11:20 pm - 3:25 pm-
17h 05m
$620Avianca
Wed, Aug 26 - Fri, Aug 28
Avianca Logo
9:25 am - 9:20 pm-
10h 55m
Avianca Logo
11:20 pm - 8:50 am-
10h 30m
$620Avianca
Booking Insights

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

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

How much is a round-trip flight from San José to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San José to Chicago O'Hare Intl Airport departing in October.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from San José usually cost between $430 and $564 in October.
The lowest price found in the past 5 days was $381 on Copa Airlines (Oct 15-Oct 20).

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

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

When flying from San José to Chicago O'Hare Airport, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to San José, you’ll find the best rates on Tuesdays and the most expensive ones on Saturdays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San José 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 from San José to Chicago O'Hare Intl Airport is February, where tickets cost $389 (return) on average. On the other hand, the most expensive months are July and March, where the average cost of round-trip tickets is $642 and $559 respectively.

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

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 $518 on average.

How far in advance should I book a flight from San José 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 from San José 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 on the flight from San José to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Expert advice

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

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Mark Chesnut

Mark Chesnut

Expert on SJO

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.

Good to know

Low season

June

Cheapest flight

$182
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San José to Chicago O'Hare Airport

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

Are your dates flexible? Find out the best times to travel from San José to O'Hare Intl 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 San José to Chicago O'Hare Airport flights

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

    In the last 5 days, the lowest price for a flight from San José to Chicago O'Hare Intl Airport was $182 for a one-way ticket and $381 for a round-trip.

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

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

  • Which airports will I be using when flying from San José to Chicago O'Hare Airport?

    San José airport is called San José Juan Santamaria Intl and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

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

    Iberia, Air Canada, GOL, and Alaska Airlines offer inflight Wi-Fi service on the San José to Chicago O'Hare Airport flight route.

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

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

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

    oneworld, and Star Alliance are the airline alliances operating flights between San José and Chicago O'Hare Airport, with oneworld being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from San José to Chicago are Copa Airlines and United Airlines. With an average price for the route of $494 and an overall rating of 7.6, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $489 and an overall rating of 7.4.

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San José 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 from San José 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 San José 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 to San José with another airline. Booking your flights between San José and ORD 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 San José 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 from San José 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 San José to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $264 or less one-way and $491 or less round-trip.

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

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

Direct departures

San José Juan Santamaria Intl to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top 4 airlines serving from San José to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from San José to Chicago. 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 San José to O'Hare Intl? 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 1564 reviews
8.1Crew
7.4Comfort
6.8Entertainment
7.8Boarding
6.9Food
Airline reviews

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

4.0 OkayAnonymous, Jun 2026
Read more Copa Airlines reviews

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.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

Copa stranded us ans then tried to charge us thousands to leave Panama.

Friendly flight team and seamless travel from one stop to next.

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

Just a minor inconvinient with weather delay! but not Copa's fault

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

The employees at the gate were not communicating, they preferred to give the upgrade to pilots and not to the elite passengers Every flight I more disappointing, clients shooed be priority instead of other employees even if they are pilots, there was plenty room for pilots in economy

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

The incoming plane was late and no information was shared. They even announced we would board in 10 muntes 40 minutes prior to the plane arriving, and the website said until takeoff that we had taken off an hour earlier

Everything you need to know for your flight from San José to O'Hare Intl

Information on your arrival and departure airports