SJO - CHI

$162 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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

 
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 (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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San José to Chicago

Thu, Aug 14 - Tue, Aug 19
Avianca Logo
8:00 pm - 2:25 pmSJO-ORD
17h 25m2 stops
Avianca Logo
8:50 am - 11:35 pmORD-SJO
15h 45m2 stops
$165Avianca
Find Deal
Thu, Aug 7 - Thu, Aug 14
Avianca Logo
8:00 pm - 2:25 pmSJO-ORD
17h 25m2 stops
Avianca Logo
8:52 am - 11:35 pmORD-SJO
15h 43m2 stops
$182Avianca
Find Deal
Wed, Oct 29 - Mon, Nov 3
Copa Airlines Logo
5:50 pm - 1:42 pmSJO-ORD
18h 52m1 stop
Copa Airlines Logo
3:10 pm - 8:01 amORD-SJO
16h 51m1 stop
$294Copa Airlines
Find Deal
Sat, Oct 4 - Sun, Oct 12
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
$309Copa Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
Spirit Airlines Logo
12:23 pm - 12:08 pmSJO-ORD
22h 45m2 stops
Spirit Airlines Logo
8:53 pm - 12:18 pmORD-SJO
15h 25m2 stops
$311Spirit Airlines
Find Deal
Fri, Jul 11 - Tue, Jul 15
Spirit Airlines Logo
12:16 pm - 11:53 pmSJO-ORD
10h 37m1 stop
Spirit Airlines Logo
5:05 am - 11:11 amORD-SJO
7h 06m1 stop
$314Spirit Airlines
Find Deal
Wed, Jul 23 - Sun, Jul 27
American Airlines Logo
6:18 am - 7:35 pmSJO-ORD
12h 17m1 stop
American Airlines Logo
5:15 am - 1:20 pmORD-SJO
9h 05m1 stop
$358American Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
6:00 am - 7:05 pmSJO-ORD
12h 05m2 stops
American Airlines Logo
5:15 am - 1:00 pmORD-SJO
8h 45m2 stops
$371American Airlines
Find Deal
Sat, Aug 2 - Sat, Aug 9
United Airlines Logo
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
United Airlines Logo
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$443United Airlines
Find Deal
Sat, Aug 2 - Sat, Aug 9
United Airlines Logo
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
United Airlines Logo
2:26 pm - 10:39 pmORD-SJO
9h 13m1 stop
$447United Airlines
Find Deal
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 75 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. It runs 24/7 and costs $5 one-way, taking 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 $378 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 $378.

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 Tuesday 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 $413 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $561 and $524 respectively.

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$162
Best time to beat the crowds with an average 4% 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 to Chicago?

    In the last 3 days, the lowest price for a flight from San José to Chicago was $162 for a one-way ticket and $165 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?

    All the following airlines offer inflight Wi-Fi service on the San José to Chicago flight route: Air Canada, American Airlines, Iberia, Lufthansa, Delta, and Alaska Airlines.

  • 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 $579 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 $522 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 $237 or less one-way and $432 or less round-trip.

Prefer to fly direct from San José to Chicago?

 
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.
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

Reviews of the 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 4278 reviews
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

We had a five hour layover in the way home from Colombia. I read the "bout your flight" email carefully before we checked bags. We had to go through security right at the gate. Almost lost our ground coffee because that airport only allows 16 ounce of coffee and we had 18. I've been to 48 countries and never heard of a coffee restriction. I can't follow a rule I don't know about. I requested they bring our coffee to our checked luggage. Instead tey gate checked our bag for free. Back to planning transfers in Dallas I guess

It was ok. However, the food was quite poor since I don't eat pasta.

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

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

The flight was delayed twice and I could not speak with anyone at the airport about checking in. The phone number to Copa - the customer service agents were polite. They are just limited at helping because they are not at the airport

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 🙃

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

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

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

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

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

The first flight was better in terms of the aircraft.

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

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

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.

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

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

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

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

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

Everything you need to know for your flight from San José to Chicago

Information on your arrival and departure airports

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