SJO - CHI

$152 Find Cheap Flights from San José to Chicago

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 5/31. 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.
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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.
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Flights Deals

Cheap Flights from San José to Chicago

 
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.

Recent round-trip flight deals from San José to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from San José to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
12:28 pm - 11:04 pmSJO-ORD
9h 36m1 stop
Spirit Airlines Logo
7:35 pm - 11:33 amORD-SJO
16h 58m1 stop
$248Spirit Airlines
Find Deal
Mi, Mai 21 - So, Mai 25
Spirit Airlines Logo
12:28 pm - 11:04 pmSJO-ORD
9h 36m1 stop
Spirit Airlines Logo
4:35 pm - 11:33 amORD-SJO
19h 58m2 stops
$257Spirit Airlines
Find Deal
Mi, Mai 21 - So, Mai 25
Copa Airlines Logo
4:10 am - 1:42 pmSJO-ORD
8h 32m1 stop
Copa Airlines Logo
7:54 am - 9:53 pmORD-SJO
14h 59m1 stop
$311Copa Airlines
Find Deal
Do, Aug 28 - Di, Sep 2
Avianca Logo
3:05 pm - 2:25 pmSJO-ORD
22h 20m2 stops
Avianca Logo
5:25 pm - 7:40 amORD-SJO
15h 15m2 stops
$316Avianca
Find Deal
Do, Aug 21 - Do, Aug 28
Avianca Logo
5:45 am - 2:25 pmSJO-ORD
7h 40m1 stop
Avianca Logo
3:45 pm - 11:15 amORD-SJO
20h 30m2 stops
$323Avianca
Find Deal
Mi, Jun 18 - Mi, Jul 2
Copa Airlines Logo
6:07 pm - 1:42 pmSJO-ORD
18h 35m1 stop
Copa Airlines Logo
3:07 pm - 8:20 amORD-SJO
18h 13m1 stop
$332Copa Airlines
Find Deal
Fr, Okt 10 - Do, Okt 16
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
5:05 am - 12:45 pmMDW-SJO
8h 40m1 stop
$426Southwest
Find Deal
Do, Sep 11 - Mo, Sep 15
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
9:00 am - 6:55 pmMDW-SJO
10h 55m2 stops
$430Southwest
Find Deal
Do, Aug 28 - Di, Sep 2
United Airlines Logo
7:55 am - 9:40 pmSJO-ORD
12h 45m1 stop
United Airlines Logo
6:00 am - 12:26 pmORD-SJO
7h 26m1 stop
$438United Airlines
Find Deal
Fr, Aug 29 - Mi, Sep 3
United Airlines Logo
1:30 pm - 12:15 amSJO-ORD
9h 45m1 stop
United Airlines Logo
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$439United Airlines
Find Deal
Mi, Mai 21 - So, Mai 25
Expert advice

Expert advice for your flight from San José to Chicago

 
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.
Airports
SJO

SJO offers free WiFi and self-check-in kiosks. Arrive early as security lines can vary in length.

Read more about SJOby Mark Chesnut
ORD

Take the CTA Blue Line from ORD to downtown Chicago for $5. It runs 24/7 and takes about 45 minutes.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on 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
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
Useful Info

KAYAK's insights & trends for San José to Chicago flights

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 to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from San José to Chicago.

Our data shows that the cheapest route for a return flight from San José to Chicago cost $272 and was between San José (SJO) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $272.

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

The average price of all round-trip flights from San José 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 to Chicago?

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, 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 is August, where tickets cost $396 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $561 and $558 respectively.

Can I save money by flying with a layover from San José to Chicago?

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.

No, with an average price for the route of $619, prices are generally cheapest when you fly direct.

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

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, 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, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonFebruary
High seasonOctober
Cheapest flight$152
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 17% 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 to Chicago?

    In the last 3 days, the lowest price for a flight from San José to Chicago was $152 for a one-way ticket and $248 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?

    Iberia, Delta, Alaska Airlines, Lufthansa, and Air Canada 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 Boeing 737 MAX 8 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, and Sunday.

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

    The two airlines most popular with KAYAK users for flights from San José to Chicago are Southwest and Delta. With an average price for the route of $588 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $584 and an overall rating of 8.0.

  • 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.

KAYAK’s 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 $255 or less one-way and $478 or less round-trip.

Prefer to fly direct from San José to Chicago?

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

Direct departures

San José Juan Santamaria Intl to Chicago

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

Sunday

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.
8.0
SouthwestOverall score based on 4294 reviews
7.6Entertainment
8.0Comfort
8.2Boarding
8.6Crew
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

I upgraded myself to Business Class at the last minute so I had a DREAMS window seat. Seeing as I've never flown Business before everything was novel and fun for me and it made the 7 hour flight much more enjoyable for sure.

It was reasonably comfortable trip considering its duration (7 hours). Crew was very good and friendly, seats very more comfortable than other planes. Only negative comment would be that the bathroom light did not get its full brightness 🙃

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

It was good, plane is a bit older so seats are somewhat flat

Great from check in all the way to the end. Very happy with Copa

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

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

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

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

I love United was disappointed we had a two hour delay, however the Pilot did say safety first.

Since when do I have to pay for my checked bag? I have a United Explorer mileage plus silver card and I was charged for my checked bags. This also is an international flight. So I would like an explanation to be clear before I choose an airline please?

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

When I'm on a 5hr 22 minute flight I expect food to be purchased. Especially when American makes a very tight connection time where u have to run to make the long flight. Chips and nuts are unacceptable and being told you should be in first class to get a meal is also unacceptable. I didn't change the flight times American Airlines did.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Don't charge so much for the luggage. Bis so much

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

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