SJO - ORD

$183 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 7/13. 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

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$385
Typical prices: $489-$294
JetBlue
Tue 9/1Tue 9/8
SJO - ORD • 1 stop
Cheapest non-stop
$526
United Airlines
Sat 10/31Sat 11/7
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 5h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $385 (round-trip)
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $431 (round-trip)
Shortest trip • 7h 23m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 94% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 20% price drop
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

Tue, Sep 1 - Tue, Sep 8
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$385JetBlue
Tue, Sep 1 - Tue, Sep 8
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$396JetBlue
Tue, Sep 1 - Tue, Sep 8
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$399JetBlue
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$420JetBlue
Thu, Oct 15 - Tue, Oct 20
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
Multiple Airlines Logo
1:49 pm - 11:59 pm
ORD
-
SJO
11h 10m
1 stop
$434Multiple Airlines
Tue, Jul 21 - Sat, Jul 25
Avianca Logo
7:45 pm - 7:27 am
SJO
-
ORD
10h 42m
2 stops
Avianca Logo
5:15 pm - 11:40 pm
ORD
-
SJO
7h 25m
1 stop
$454Avianca
Thu, Oct 15 - Tue, Oct 20
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
Multiple Airlines Logo
1:49 pm - 11:59 pm
ORD
-
SJO
11h 10m
1 stop
$456Multiple Airlines
Tue, Sep 15 - Mon, Sep 28
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
Multiple Airlines Logo
2:53 am - 11:59 pm
ORD
-
SJO
22h 06m
1 stop
$457Multiple Airlines
Tue, Sep 15 - Mon, Sep 28
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
Multiple Airlines Logo
2:53 am - 11:59 pm
ORD
-
SJO
22h 06m
1 stop
$458Multiple Airlines
Wed, Sep 16 - Sat, Sep 19
Copa Airlines Logo
4:08 am - 1:02 am
SJO
-
ORD
19h 54m
1 stop
Copa Airlines Logo
8:01 am - 7:10 am
ORD
-
SJO
24h 09m
1 stop
$459Copa 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 September.

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 Tuesday 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 $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 $617 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 seasonJune
Cheapest flight$183
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 3% 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 $183 for a one-way ticket and $385 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, Alaska Airlines, and American 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 oneworld are the airline alliances operating flights between San José and Chicago O'Hare Airport, with Star Alliance being the most commonly used for this route.

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

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

  • 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 $498 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 $479 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 $353 or less one-way.

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 1567 reviews
6.8Entertainment
7.4Comfort
6.9Food
8.1Crew
7.8Boarding
Airline reviews

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.

6.0 GoodAnonymous, May 2026
PTY - LAX
Read more Copa Airlines reviews

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.

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Avoid at all costs. My wife had to stay back on a connecting flight as her parents flight was delayed. 10 days later on the way back they cancelled all our flights. We had to rebook all four of us on the next days flight.

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

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

Copa staff at PTY and one particular crew member were unhelpful & rude.

Seats were awful. Media should have been included for such a long flight.

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.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

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 actually upgraded to the medium level of seats from basic and even doing that it may have been physically the most uncomfortable flight I have ever had. They packed everyone like is a train to death camp. It was a red eye so I hoped to get some sleep but it was physically impossible to find a comfortable way to rest. I met other folks on the same flight and they said the same thing. It was an utterly miserable flight and if I have any other options I will never fly with them again

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

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

No free snacks nor drinks on very short 30min flight. Entertainment system is over wifi to your own phone or tablet, which is good but often a show or movie just stops and refuses to continue

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

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

Information on your arrival and departure airports