SJO - CHI

$174 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
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
$357
Typical prices: $653-$437
Multiple Airlines
Fri 7/17Fri 7/31
SJO - ORD • 1 stop
Cheapest non-stop
$618
Typical prices: $740-$542
United Airlines
Sat 5/2Sat 5/9
SJO - ORD • Non-stop
Advice from real travelers
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
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 5h 35m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top airlines
Cheapest • from $361 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $291 (round-trip)
Shortest trip • 7h 40m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 94% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
Good to know
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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

Fri, Jul 17 - Fri, Jul 31
Multiple Airlines Logo
1:21 pm - 12:25 pm
SJO
-
ORD
22h 04m
1 stop
Multiple Airlines Logo
5:10 am - 12:15 pm
ORD
-
SJO
8h 05m
1 stop
$357Multiple Airlines
Thu, Aug 27 - Sun, Aug 30
Multiple Airlines Logo
9:35 am - 11:14 pm
SJO
-
ORD
12h 39m
1 stop
Multiple Airlines Logo
5:10 am - 12:15 pm
ORD
-
SJO
8h 05m
1 stop
$360Multiple Airlines
Sat, Jul 18 - Sat, Jul 25
Spirit Airlines Logo
1:21 pm - 11:59 pm
SJO
-
ORD
9h 38m
1 stop
Spirit Airlines Logo
7:07 pm - 12:15 pm
ORD
-
SJO
18h 08m
1 stop
$361Spirit Airlines
Fri, May 15 - Sat, May 16
Multiple Airlines Logo
1:00 pm - 11:15 pm
SJO
-
ORD
9h 15m
1 stop
Multiple Airlines Logo
1:59 pm - 11:45 am
ORD
-
SJO
22h 46m
2 stops
$362Multiple Airlines
Thu, May 14 - Sun, May 17
Spirit Airlines Logo
1:00 pm - 11:15 pm
SJO
-
ORD
9h 15m
1 stop
Spirit Airlines Logo
5:05 am - 11:45 am
ORD
-
SJO
7h 40m
1 stop
$367Spirit Airlines
Mon, Oct 19 - Wed, Oct 28
Copa Airlines Logo
10:03 am - 12:57 am
SJO
-
ORD
13h 54m
1 stop
Copa Airlines Logo
3:13 pm - 8:21 am
ORD
-
SJO
18h 08m
1 stop
$368Copa Airlines
Sat, Jul 11 - Sat, Jul 25
Delta Logo
1:16 pm - 10:15 pm
SJO
-
MDW
7h 59m
1 stop
Delta Logo
6:00 am - 11:51 am
MDW
-
SJO
6h 51m
1 stop
$476Delta
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
8:45 am - 9:35 pm
SJO
-
MDW
11h 50m
2 stops
Southwest Logo
6:30 am - 7:40 pm
MDW
-
SJO
14h 10m
2 stops
$535Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
8:45 am - 9:35 pm
SJO
-
MDW
11h 50m
2 stops
Southwest Logo
1:10 pm - 7:40 pm
MDW
-
SJO
7h 30m
1 stop
$554Southwest
Thu, May 28 - Wed, Jun 3
Delta Logo
1:20 pm - 8:43 am
SJO
-
MDW
18h 23m
2 stops
Delta Logo
1:22 pm - 11:52 am
MDW
-
SJO
23h 30m
2 stops
$562Delta
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 July.

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 $313 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 November, where tickets cost $111 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $194 and $192 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 3 weeks before departure, which saves you about 7% 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.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Mark Chesnut

Mark Chesnut

Expert on SJO

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.

Good to know

Low seasonFebruary
Cheapest flight$174
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 9% 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 $173 for a one-way ticket and $357 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?

    Air Canada, American Airlines, Iberia, GOL, 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?

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

  • Which is the best airline for flights from San José to Chicago, 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 $505 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 $589 and an overall rating of 7.9.

  • 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 $230 or less one-way and $406 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

See more direct flights

Direct returns

Chicago to San José Juan Santamaria Intl

Saturday

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 4314 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

Copa staff at PTY and one particular crew member were unhelpful & rude.

Seats were awful. Media should have been included for such a long flight.

A lot things happened in this trip.The fly should be less stress.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

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.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

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

Information on your arrival and departure airports