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SJO - CHI

Find cheap flights from San José to Chicago from $119

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 Chicago departing on 5/24. 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
0 bags
Sun 5/19
Sun 5/26

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Chicago.
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

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Cheap flight deals from San José to Chicago (SJO-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San José to Chicago 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 and deals for you by selecting your travel dates.
Choose your dates
9:21 am - 9:27 pmSJO-MDW
11h 06m1 stop
7:00 am - 8:11 amMDW-SJO
26h 11m1 stop
$170Frontier
Find Deal
Thu, May 2 - Wed, May 8
12:32 pm - 4:35 pmSJO-ORD
27h 03m1 stop
5:41 pm - 12:04 amORD-SJO
7h 23m1 stop
$215Spirit Airlines
Find Deal
Thu, May 9 - Tue, May 14
1:42 pm - 11:52 pmSJO-ORD
9h 10m1 stop
6:10 am - 12:04 amORD-SJO
18h 54m2 stops
$216Spirit Airlines
Find Deal
Wed, May 22 - Tue, May 28
1:42 pm - 11:52 pmSJO-ORD
9h 10m1 stop
5:33 pm - 9:21 amORD-SJO
16h 48m1 stop
$217Spirit Airlines
Find Deal
Wed, May 22 - Sun, May 26
9:36 am - 11:29 pmSJO-ORD
12h 53m1 stop
5:41 pm - 12:04 amORD-SJO
7h 23m1 stop
$218Spirit Airlines
Find Deal
Wed, May 8 - Tue, May 14
9:21 am - 9:38 pmSJO-MDW
35h 17m2 stops
7:00 am - 8:11 amMDW-SJO
26h 11m1 stop
$229Frontier
Find Deal
Thu, May 2 - Wed, May 8
1:13 pm - 9:41 pmSJO-MDW
7h 28m1 stop
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$667Delta
Find Deal
Mon, Jul 29 - Mon, Aug 12
7:00 am - 5:59 pmSJO-MDW
9h 59m1 stop
9:28 am - 8:27 pmMDW-SJO
11h 59m2 stops
$686Delta
Find Deal
Fri, Jun 14 - Sat, Jun 22
7:00 am - 5:59 pmSJO-MDW
9h 59m1 stop
6:00 am - 8:27 pmMDW-SJO
15h 27m1 stop
$828KLM
Find Deal
Thu, Jun 27 - Fri, Jul 5
7:46 am - 9:44 pmSJO-MDW
12h 58m2 stops
6:00 am - 11:36 pmMDW-SJO
18h 36m2 stops
$1,237Aeromexico
Find Deal
Thu, Oct 10 - Tue, Oct 15

Flights from San José to Chicago - Travel Insights & Trends

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

What is the cheapest San José, San José Province to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from San José, San José Province to Chicago.
Our data shows that the cheapest route for a one-way flight from San José, San José Province to Chicago cost $281 and was between San José, San José Province and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $408.

What’s the cheapest day of the week to fly from San José to Chicago?

The average price of all flights from San José, San José Province to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San José to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Saturdays for the best deals.

What is the cheapest month to fly from San José, San José Province to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San José, San José Province to Chicago, 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, San José Province to Chicago is August, where tickets cost $290 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $601 and $574 respectively.

How far in advance should I book a flight from San José, San José Province to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San José, San José Province to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from San José, San José Province to Chicago, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 69 days before departure.

Which airlines provide the cheapest flights from San José to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting San José to Chicago were found on Frontier ($170) and Spirit Airlines ($215). Spirit Airlines proposed the cheapest one-way flight at $119.

Which airlines fly non-stop between San José, San José Province and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San José, San José Province to Chicago.
There is just one airline that flies from San José, San José Province to Chicago direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $651.

How many flights are there between San José, San José Province and Chicago per day?

There is a maximum of 1 nonstop flight a day that takes off from San José, San José Province and lands in Chicago, with an average flight time of 5h 28m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 1 flights.

Which cabin class options are there for flights between San José, San José Province and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from San José to Chicago take?

Nonstop flights from San José generally make it to Chicago in 5h 28m. The flying distance between the two cities is 2,211 miles.

What’s the earliest departure time from San José to Chicago?

Early birds can take the earliest flight from San José, San José Province at 1:00 pm and will be landing in Chicago at 7:28 pm.

What’s the latest departure time from San José to Chicago?

If you prefer to fly at night, the latest flight from San José, San José Province to Chicago jets off at 1:00 pm and lands at 7:28 pm.

Good to know

Low season

February

High season

October

Cheapest flight

$119
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from San José to Chicago O'Hare Airport

When to book flights from San José to Chicago

Are your dates flexible? Find out the best times to travel from San José to Chicago 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 flights from San José to Chicago

  • What is the cheapest flight from San José, San José Province to Chicago?

    In the last 3 days, the lowest price for a flight from San José, San José Province to Chicago was $119 for a one-way ticket and $170 for a round-trip.

  • Do I need a passport to fly between San José and Chicago?

    Yes, you’ll need a passport to travel to Chicago from San José.

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

    Lufthansa, Delta, and Alaska Airlines offer inflight Wi-Fi service on the San José to Chicago flight route.

  • Which aircraft models fly most regularly from San José to Chicago?

    The Airbus A350-900 is the aircraft model that flies most regularly on the San José to Chicago flight route.

  • Which airline alliances offer flights from San José to Chicago?

    Star Alliance is the only airline alliance operating flights between San José and Chicago.

  • On which days can I fly direct from San José to Chicago?

    You can catch a nonstop flight from San José to Chicago on on Saturday.

  • Which is the best airline for flights from San José to Chicago, Delta or Aeromexico?

    The two airlines most popular with KAYAK users for flights from San José to Chicago are Delta and Aeromexico. With an average price for the route of $705 and an overall rating of 8.0, Delta is the most popular choice. Aeromexico is also a great choice for the route, with an average price of $627 and an overall rating of 7.6.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to San José with another airline.

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

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

See more FAQs

Top tips for finding a cheap flight from San José to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $344 or less one-way and $446 or less round-trip.

Prefer to fly non-stop from San José to Chicago?

Find which airlines fly direct from Juan Santamaria Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

San José Juan Santamaria Intl to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

Nonstop returns

Chicago to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from San José to Chicago

 
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 Chicago? 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.
7.8
Copa AirlinesOverall score based on 2932 reviews
8.3crew
8.1boarding
7.2entertainment
7.4food
7.7comfort
Airline reviews

Captain and Crew were excellent. The Boeing 737-800 was showing its age. In flight entertainment system was sluggish and my Business Class seat on the outbound flight had some mechanical issues. Only real problem was the location of the Gate in Panama PTY. It was a 40 minute hike from Security to the Gate. There should have been some sort of warning about the distance.

10.0 ExcellentAnonymous, Mar 2024PTY - BWI
Read more about Copa Airlines reviews

Captain and Crew were excellent. The Boeing 737-800 was showing its age. In flight entertainment system was sluggish and my Business Class seat on the outbound flight had some mechanical issues. Only real problem was the location of the Gate in Panama PTY. It was a 40 minute hike from Security to the Gate. There should have been some sort of warning about the distance.

landed in panama it was in terminal one. We had to take a bus to terminal two for customs. Then back to terminal one. It was very frustrating. Then, on the way back from panama it was the same situation. We had to go back and forth between terminals to check in and drop our bags and then to board. When we were leaving, we had to wait in line for the boarding area and go through another gate security process. They told the bottles of water and coffee were bought while in line in the airport after we passed the main security. Ridiculous (and expensive). A much better communication system is needed.

This was my first time flying Copa but I'll definitely be back! Great service, professional agents, and delicious food for a fair price. Thanks for a great trip!

Horrible experience from start to end. Copa costumer service is non existent. They treat you bad. Everybody tells you different information. We didn’t received our luggage in the 1 day stop we did even we they said if was not going to be a problem. They didn’t respect the seats that we had and spread our family leaving in between of two big people who didn’t leave any space for me and crush me from side to side. I’ll never recommend Copa to anybody.

No cumpli mencionado trayecto por reasignacion de Copa Pero extraviaron mis maletas por su culpa

I was fortunate enough to have an entire row to myself and that was the highlight. Unfortunately, the flight was really turbulent which had no impact on how effective the crew was. However, I am disabled and should have boarded the flight first, but that wasn't the case. They also decided to take my bag at the gate because I had one too many and upon my picking it up at JFK it along with my rollator had been damaged. I am a vegan so the didn't have a proper meal for me and I was unable to view the entertainment because I didn't receive a set of headphones and if I needed to supply my own I wasn't made aware of that either. The crew was great, but overall everything was pretty lackluster.

Pros: "Nothing. This airline is awful in every way imaginable."
Cons: "We booked tickets to Costa Rica with Copa and they just changed our flights to two days later than the booking. They didn’t even bother to inform us of the change we only found out because we booked through Kayak and they let us know. Apparently Copa expects you to frequently check your booking just in case they’ve changed anything and don’t feel the need to inform their customers of any changes they make. Then we were told we could get a Copa voucher to use for other Copa flights for having to cancel our booking and rebook with another airline as a 48 hour change to our flight made flying with Copa not doable for us. But the website kept telling us we had a voucher that was sent to our email but despite repeated attempts it never came through. And spent hours trying to get through to someone on the phone to sort it out with no success ever getting through. My advice. NEVER EVER FLY WITH COPA."
Pros: "Both of my flights were on time which i know sounds basic but all of the flights i’ve catched from SJO to X were late and this time my connection in Panama was only 1h15 and we got there earlier, so that was nice!"
Cons: "A bunch of seats were free and we were mostly sat all together (3 person next to each other).. With the covid situation i think it could be good to be more separate if possible"
Cons: "Sure. I had booked a two week vacation in Brazil. All hotels, car rental and guides booked. Copa changed my fligjt at the last minute and out of the 14 days vacatipn I had in Brazil, they would have me spend 6 days in Panama City!!! Lost of small fortune with hotels, car rentals amd had to buy another ticket with Latam. They are a scam!!"
Cons: "Due the COVID-19 El Salvador closed its boarders, leaving me unable to fly. I have sent two emails, called and spoke to a customer service representative who treated me unprofessionally and rude. After that I have been calling numerous times with a wait of over 25 minutes each time and I still have to answer from you as a company. I am extremely disappointed and want an answer soon."

I did not like anything, first time I use company and for sure it will be the last time, they charge for simple operations that any other average airline wouldn't charge.

The good thing is the flight was on time and the crew was really nice. They can work better the arriving with staff

The inflight entertainment did not work on a 6 hour flight The cel phone chargers did not work There was a 45 minute wait for the luggage to get off the plane.

Seat space was terrible no food on a six hour flight

There was no bag included in the reservation. The price was double. Not properly advertised

There is no food. There is no in-inflight entertainment. The seats are cardboard. The airline is a living hellscape.

They could offer free food and drink like other international flights.

Flight attendants to show up on time, offer drinks and food.

The worst airline, the crew so mean and rude, everything was a nightmare, if I start to write, I'll never end

Pros: "Comfortable flight good crew"
Cons: "The boarding process could use help, to chaotic at times but some of the has to do with the countries policies. But I’d give it a B+"

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

Book cheap flights from San José to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San José to Chicago found on KAYAK in the last 72 hours.
5/24Fri
1 stopSpirit Airlines
15h 41mSJO-ORD
$119
6/7Fri
1 stopSpirit Airlines
9h 02mSJO-ORD
$123
5/8Wed
1 stopSpirit Airlines
14h 36mSJO-ORD
$132
6/28Fri
1 stopAvianca
7h 55mSJO-ORD
$283
6/7Fri
nonstopAvianca
7h 55mSJO-ORD
$289
9/1Sun
1 stopFrontier
10h 09mSJO-MDW
$315
5/25Sat
2 stopsAmerican Airlines
12h 24mSJO-ORD
$406
5/25Sat
nonstopUnited Airlines
5h 28mSJO-ORD
$430
7/1Mon
2 stopsAmerican Airlines
14h 12mSJO-ORD
$470
5/4Sat
nonstopUnited Airlines
5h 28mSJO-ORD
$530

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Last minute flights from San José to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from San José to Chicago that are departing in the next 10 days.
4/24Wed
multi-stopSpirit Airlines
14h 54mSJO-ORD
5/1Wed
multi-stopSpirit Airlines
16h 48mORD-SJO
$304
4/24Wed
multi-stopSpirit Airlines
14h 54mSJO-ORD
5/1Wed
multi-stopSpirit Airlines
16h 48mORD-SJO
$341
4/24Wed
multi-stopSpirit Airlines
14h 54mSJO-ORD
5/1Wed
multi-stopSpirit Airlines
16h 33mORD-SJO
$355
4/22Mon
multi-stopUnited Airlines
12h 28mSJO-ORD
4/29Mon
multi-stopUnited Airlines
11h 47mORD-SJO
$989
4/20Sat
nonstopUnited Airlines
5h 28mSJO-ORD
5/5Sun
multi-stopUnited Airlines
9h 52mORD-SJO
$1,017
4/22Mon
multi-stopDelta
14h 14mSJO-MDW
4/29Mon
multi-stopDelta
6h 52mMDW-SJO
$1,018
4/20Sat
multi-stopAmerican Airlines
12h 20mSJO-ORD
5/5Sun
multi-stopAmerican Airlines
8h 20mORD-SJO
$1,029
4/22Mon
multi-stopAmerican Airlines
10h 37mSJO-ORD
4/29Mon
multi-stopAmerican Airlines
8h 20mORD-SJO
$1,058
4/20Sat
multi-stopAeromexico
9h 47mSJO-ORD
5/4Sat
multi-stopAeromexico
10h 47mORD-SJO
$1,212
4/22Mon
multi-stopAeromexico
46h 04mSJO-ORD
4/29Mon
multi-stopAeromexico
22h 52mORD-SJO
$1,221

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San José - Chicago Flights

Departure:

San José (SJO)Costa Rica

Return flight deals:

Chicago - San José

Cabin classes:

$3,499
$408