SJO - CHI

$116 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 2/9. 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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Everything you should know

Cheapest round-trip
$266
Typical prices: $312-$527
Spirit Airlines
Fri 2/6Sun 2/15
SJO - ORD • 1 stop
Cheapest non-stop
$340
Typical prices: $426-$613
United Airlines
Thu 1/22Mon 1/26
SJO - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 $266 (round-trip)
Southwest
Best reviews • 7.9 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 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 16% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
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

Fri, Feb 6 - Sun, Feb 15
Spirit Airlines Logo
1:30 pm - 11:46 pm
SJO
-
ORD
10h 16m1 stop
Spirit Airlines Logo
3:28 pm - 11:40 am
ORD
-
SJO
20h 12m2 stops
$266Spirit Airlines
Thu, Feb 5 - Sun, Feb 22
Spirit Airlines Logo
1:30 pm - 11:46 pm
SJO
-
ORD
10h 16m1 stop
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m1 stop
$267Spirit Airlines
Thu, Feb 5 - Sun, Feb 22
Spirit Airlines Logo
12:33 pm - 11:46 pm
SJO
-
ORD
11h 13m2 stops
Spirit Airlines Logo
3:28 pm - 11:40 am
ORD
-
SJO
20h 12m2 stops
$271Spirit Airlines
Wed, Feb 25 - Mon, Mar 2
Volaris Logo
2:50 pm - 4:36 am
SJO
-
ORD
13h 46m1 stop
Volaris Logo
12:59 pm - 12:07 am
ORD
-
SJO
11h 08m1 stop
$273Volaris
Tue, Feb 3 - Fri, Feb 6
Spirit Airlines Logo
12:33 pm - 11:46 pm
SJO
-
ORD
11h 13m2 stops
Spirit Airlines Logo
8:43 pm - 12:22 pm
ORD
-
SJO
15h 39m1 stop
$276Spirit Airlines
Fri, Feb 20 - Sun, Mar 1
Multiple Airlines Logo
12:35 pm - 2:55 pm
SJO
-
MDW
26h 20m1 stop
Multiple Airlines Logo
6:15 am - 3:30 pm
MDW
-
SJO
9h 15m1 stop
$299Multiple Airlines
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$302Frontier
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$333Frontier
Wed, Feb 25 - Mon, Mar 2
Multiple Airlines Logo
3:05 pm - 1:56 pm
SJO
-
MDW
22h 51m2 stops
Multiple Airlines Logo
9:32 pm - 11:40 am
MDW
-
SJO
14h 08m1 stop
$363Multiple Airlines
Thu, Feb 5 - Sun, Feb 22
Southwest Logo
1:45 pm - 10:25 pm
SJO
-
MDW
8h 40m1 stop
Southwest Logo
6:05 am - 12:50 pm
MDW
-
SJO
6h 45m1 stop
$382Southwest
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 February.

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 $224 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 Tuesday, 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 January, where tickets cost $379 (return) on average. On the other hand, the most expensive months are April and June, where the average cost of round-trip tickets is $489 and $487 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 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Expert advice

Expert advice for your flight from San José to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
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.

ORD

Take the CTA Blue Line from ORD to downtown Chicago. It runs 24/7 and costs $5 one-way, taking about 45 minutes.

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$116
Best time to beat the crowds but there is an average 4% increase 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 $116 for a one-way ticket and $266 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, Alaska Airlines, and Iberia 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 9 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 $519 and an overall rating of 7.9, Southwest is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $466 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 $149 or less one-way and $367 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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.

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

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

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

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

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.

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

Information on your arrival and departure airports