SJO - ORD

$134 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$263
Typical prices: $317-$502
Spirit Airlines
Thu 2/19Tue 2/24
SJO - ORD • 2 stops
Cheapest non-stop
$295
Typical prices: $346-$574
American Airlines
Thu 2/12Tue 2/24
SJO - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Top airlines
Spirit Airlines
Cheapest • from $263 (round-trip)
Copa Airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 14% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 14% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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, Feb 19 - Tue, Feb 24
Spirit Airlines Logo
1:31 pm - 7:54 am
SJO
-
ORD
18h 23m
2 stops
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
$263Spirit Airlines
Fri, Feb 20 - Mon, Feb 23
Spirit Airlines Logo
1:31 pm - 11:47 pm
SJO
-
ORD
10h 16m
1 stop
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
$264Spirit Airlines
Wed, Mar 4 - Sun, Mar 8
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m
2 stops
Spirit Airlines Logo
8:16 pm - 11:22 am
ORD
-
SJO
16h 06m
1 stop
$265Spirit Airlines
Fri, Feb 20 - Sun, Feb 22
Spirit Airlines Logo
1:31 pm - 11:47 pm
SJO
-
ORD
10h 16m
1 stop
Spirit Airlines Logo
8:59 am - 11:40 am
ORD
-
SJO
26h 41m
2 stops
$266Spirit Airlines
Thu, Feb 12 - Tue, Feb 24
Spirit Airlines Logo
1:31 pm - 9:13 pm
SJO
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m
2 stops
$267Spirit Airlines
Sat, Feb 28 - Wed, Mar 4
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m
2 stops
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
$268Spirit Airlines
Fri, Feb 20 - Sun, Feb 22
Spirit Airlines Logo
1:31 pm - 9:13 pm
SJO
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
$269Spirit Airlines
Wed, Mar 4 - Tue, Mar 10
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m
2 stops
Spirit Airlines Logo
9:18 am - 10:40 am
ORD
-
SJO
26h 22m
2 stops
$272Spirit Airlines
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
12:35 pm - 11:38 pm
SJO
-
ORD
11h 03m
1 stop
Multiple Airlines Logo
9:18 am - 10:40 am
ORD
-
SJO
26h 22m
2 stops
$273Multiple Airlines
Sat, Feb 14 - Sat, Feb 21
Spirit Airlines Logo
1:31 pm - 11:47 pm
SJO
-
ORD
10h 16m
1 stop
Spirit Airlines Logo
4:43 pm - 12:22 pm
ORD
-
SJO
19h 39m
1 stop
$274Spirit Airlines
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 February.

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 Thursday 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 February, where tickets cost $385 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $505 and $475 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 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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 seasonFebruary
Cheapest flight$134
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 3% 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 $134 for a one-way ticket and $263 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?

    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.

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

    There are nonstop flights from San José to Chicago O'Hare Airport on a daily basis.

  • 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 $449 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 $504 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 $160 or less one-way and $298 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, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to San José Juan Santamaria Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United 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 1558 reviews
8.1Crew
6.8Food
7.4Comfort
6.8Entertainment
7.8Boarding
Airline reviews

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

6.0 GoodIrma, Jan 2026
PTY - MIA
Read more Copa Airlines reviews

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

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

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

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

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.

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

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

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.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Avianca has transitioned from full service legacy airline to "low cost" but has now became a strange hybrid (minimum leg space, started offering business class in domestic flights again, charges passenger for printing boarding pass, etc.). National and international coverage and destinations are really wide but service is not at its best

Staff are the rudest in the industry … awful customer service … will never fly Avianca again

The flight attendant smashed her beverage cart into my knee, causing significant amount of pain. The seats were extremely uncomfortable. No food or drink is offered unless you want to pay the ridiculous prices for it. The schedule of flying in the overnight hours is also very uncomfortable.

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

I like the crew they're very friendly. I don't like. on five hour flight they not offered snacks. Any drink. Not even coffee

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

Luggage lost and nowhere to be found, no response from either airline regarding my bag

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!

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

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

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

Information on your arrival and departure airports