SJO - ORD

$106 Find Cheap Flights from San José 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 from San José to O'Hare Intl departing on 10/18. 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

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 in flight searches from San José to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Chicago, as well as popular online travel agencies
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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

Wed, Oct 1 - Sat, Oct 11
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
6:58 pm - 11:30 amORD-SJO
17h 32m2 stops
$180Spirit Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
$184Spirit Airlines
Find Deal
Thu, Sep 25 - Thu, Oct 2
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
6:44 pm - 11:14 amORD-SJO
17h 30m1 stop
$192Spirit Airlines
Find Deal
Wed, Oct 1 - Sat, Oct 11
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
$193Spirit Airlines
Find Deal
Wed, Oct 8 - Thu, Oct 16
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
$195Spirit Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
5:05 am - 11:14 amORD-SJO
7h 09m1 stop
$197Spirit Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
$198Spirit Airlines
Find Deal
Tue, Sep 30 - Sun, Oct 5
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
$200Spirit Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
$202Spirit Airlines
Find Deal
Fri, Oct 10 - Sat, Oct 18
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
$204Spirit Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom on this route.
Take the CTA Blue Line from O'Hare to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 10% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$180
Overall average: $436
Spirit Airlines
Wed 10/1Sat 10/11
SJO - ORD • 1 stop
Cheapest non-stop
$325
Typical prices: $377-623
American Airlines
Fri 11/7Sun 11/9
SJO - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Expert advice

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

 
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.
Airlines
United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Wi-Fi offers free messaging; T-Mobile customers often get free streaming Wi-Fi.

American Airlines

American Airlines' Main Cabin Extra includes early boarding and complimentary alcoholic drinks.


American Airlines offers high-speed Wi-Fi for purchase; T-Mobile customers may get complimentary access.

Airports
SJO

For a smooth departure, arrive early at SJO as security lines can vary. Enjoy free WiFi and self-check-in kiosks for convenience.

Read more about SJOby Mark Chesnut
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays common with driving.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and 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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

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
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.

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 Wednesday and avoid Sundays 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 November, where tickets cost $428 (return) on average. On the other hand, the most expensive months are May and April, where the average cost of round-trip tickets is $518 and $517 respectively.

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 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$106
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 7% increase in price.
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 3 days, the lowest price for a flight from San José to Chicago O'Hare Intl Airport was $106 for a one-way ticket and $180 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?

    American Airlines, Air Canada, Iberia, 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?

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

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

    The two airlines most popular with KAYAK users for flights from San José to Chicago are Southwest and Copa Airlines. With an average price for the route of $527 and an overall rating of 8.0, Southwest is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $482 and an overall rating of 7.6.

  • 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 $224 or less one-way and $377 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

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to San José Juan Santamaria Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top 5 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 1531 reviews
8.1Crew
7.8Boarding
6.8Entertainment
6.8Food
7.4Comfort
Airline reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

10.0 ExcellentNeil, Aug 2025PTY - BGI
Read more Copa Airlines reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

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

Great experience with a crew always thinking in the passenger

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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!

No food, terms when selling are not clear. To pricy for the service in general

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

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

Boarding was excessively slow. They do it by groups in a way that it doesn’t make sense. After business class , ppl that need assistance and any other priority group they should have ppl board from the back to the front. First rows 20+. Then 15+. Then 10, etc. having ppl sitting in the back board last makes no sense. The libe backame long as soon as ppl on rows 10 or so where told to board. The line went all the way up the ramp and tunnel for 25 mins.

Flight to Bogotá delayed by 3 h Missed connection from Bogotá to Guayaquil. Avianca unable to bring us to Baltra on time Overall delay 36h. We missed boat departure from galagos. Overall 10 day trip needed to be cancelled. Avianca was completely un-professional.

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

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

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

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