SJO - CHI

$122 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 12/16. 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

 
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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Flight 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

Sat, Dec 6 - Thu, Dec 11
Spirit Airlines Logo
1:31 pm - 12:09 amSJO-ORD
10h 38m1 stop
Spirit Airlines Logo
5:00 am - 12:25 pmORD-SJO
7h 25m1 stop
$221Spirit Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$224Spirit Airlines
Find Deal
Tue, Jan 20 - Tue, Jan 27
Avianca Logo
5:00 am - 2:50 pmSJO-ORD
9h 50m1 stop
Avianca Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$264Avianca
Find Deal
Fri, Nov 14 - Tue, Nov 18
Multiple Airlines Logo
2:20 am - 3:10 pmSJO-ORD
12h 50m1 stop
Multiple Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$270Multiple Airlines
Find Deal
Sun, Nov 16 - Sun, Dec 7
Multiple Airlines Logo
1:30 pm - 11:14 amSJO-ORD
45h 44m2 stops
Multiple Airlines Logo
5:00 am - 12:25 pmORD-SJO
7h 25m1 stop
$274Multiple Airlines
Find Deal
Mon, Jan 19 - Sun, Jan 25
Avianca Logo
7:50 pm - 2:50 pmSJO-ORD
19h 00m1 stop
Avianca Logo
2:35 pm - 9:50 pmORD-SJO
7h 15m1 stop
$280Avianca
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
2:31 pm - 11:47 pmSJO-MDW
9h 16m1 stop
Delta Logo
9:34 am - 10:20 pmMDW-SJO
12h 46m2 stops
$339Delta
Find Deal
Sat, Jan 24 - Wed, Jan 28
Delta Logo
7:00 am - 3:40 pmSJO-MDW
8h 40m1 stop
Delta Logo
1:28 pm - 10:15 pmMDW-SJO
8h 47m2 stops
$343Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Southwest Logo
9:00 am - 8:25 pmSJO-MDW
11h 25m1 stop
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
$366Southwest
Find Deal
Fri, Jan 16 - Tue, Jan 20
Southwest Logo
1:45 pm - 10:25 pmSJO-MDW
8h 40m1 stop
Southwest Logo
8:55 am - 7:30 pmMDW-SJO
10h 35m1 stop
$410Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Choose Economy Plus on United for extra legroom.
Use free WiFi at SJO and arrive early for security.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Spirit Airlines
Cheapest • from $221 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
SJO-ORD
Cheapest
SJO-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 18% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 11% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$221
Overall average: $480
Spirit Airlines
Sat 12/6Thu 12/11
SJO - ORD • 1 stop
Cheapest non-stop
$323
Typical prices: $431-$633
American Airlines
Sat 12/6Thu 12/11
SJO - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

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.

How much is a round-trip flight from San José to Chicago?

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 departing in December.

What is the cheapest San José to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from San José to Chicago costs $243 on the route between San José (SJO) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 Friday, 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 November, where tickets cost $410 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $514 and $507 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, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

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.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Download the American Airlines app for inflight entertainment, as seatback screens are being removed.

United Airlines

Opt for Economy Plus for up to six inches more legroom than standard economy seats.


Check United's Wi-Fi coverage map before purchasing, as connection quality varies.

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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and 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

Good to know

Low seasonFebruary
Cheapest flight$122
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 $122 for a one-way ticket and $221 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?

    American Airlines, Air Canada, Iberia, 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 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?

    oneworld, and Star Alliance are the airline alliances operating flights between San José and Chicago, with oneworld being the most commonly used for this route.

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

    There are nonstop flights from San José to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from San José to Chicago are Southwest and Copa Airlines. With an average price for the route of $535 and an overall rating of 8.0, Southwest is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $467 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.

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 $163 or less one-way and $325 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

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to San José Juan Santamaria Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 5 airlines serving from San José to 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 4242 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

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

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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

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

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

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

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

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.

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

Information on your arrival and departure airports

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