CHI - SJO

$116 Find Cheap Flights from Chicago to San José

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San José departing on 7/8. 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 San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
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Flights Deals

Cheap Flights from Chicago to San José (CHI-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San José 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 Chicago to San José

Tue, Jul 8 - Tue, Jul 22
 Logo
10:46 am - 11:11 amORD-SJO
25h 25m2 stops
 Logo
5:05 am - 4:05 pmSJO-ORD
10h 00m1 stop
Tue, Jul 8 - Tue, Jul 22
Spirit Airlines Logo
10:46 am - 11:11 amORD-SJO
25h 25m2 stops
Spirit Airlines Logo
12:16 pm - 11:13 pmSJO-ORD
9h 57m1 stop
$298Spirit Airlines
Find Deal
Wed, Oct 8 - Mon, Oct 13
Copa Airlines Logo
7:54 am - 4:22 pmORD-SJO
9h 28m1 stop
Copa Airlines Logo
10:05 am - 12:22 amSJO-ORD
13h 17m1 stop
$310Copa Airlines
Find Deal
Tue, Nov 11 - Thu, Nov 13
Copa Airlines Logo
6:56 am - 6:56 pmORD-SJO
12h 00m1 stop
Copa Airlines Logo
4:13 am - 12:22 pmSJO-ORD
8h 09m1 stop
$325Copa Airlines
Find Deal
Wed, Aug 6 - Wed, Aug 13
American Airlines Logo
6:00 am - 8:15 pmORD-SJO
15h 15m1 stop
American Airlines Logo
1:55 pm - 10:59 pmSJO-ORD
8h 04m1 stop
$362American Airlines
Find Deal
Thu, Jul 3 - Tue, Jul 8
Avianca Logo
5:25 pm - 7:40 amORD-SJO
15h 15m2 stops
Avianca Logo
5:05 am - 4:05 pmSJO-ORD
10h 00m1 stop
$363Avianca
Find Deal
Thu, Jul 10 - Mon, Jul 14
Avianca Logo
5:25 pm - 7:40 amORD-SJO
15h 15m2 stops
Avianca Logo
7:45 pm - 4:05 pmSJO-ORD
19h 20m1 stop
$385Avianca
Find Deal
Wed, Oct 8 - Mon, Oct 13
American Airlines Logo
5:15 am - 1:00 pmORD-SJO
8h 45m2 stops
American Airlines Logo
2:25 pm - 9:02 amSJO-ORD
17h 37m1 stop
$386American Airlines
Find Deal
Mon, Sep 22 - Sun, Sep 28
Southwest Logo
8:05 am - 6:55 pmMDW-SJO
11h 50m2 stops
Southwest Logo
12:35 pm - 9:15 pmSJO-MDW
7h 40m1 stop
$407Southwest
Find Deal
Mon, Sep 1 - Tue, Sep 30
Southwest Logo
8:05 am - 6:55 pmMDW-SJO
11h 50m2 stops
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$414Southwest
Find Deal
Expert advice

Expert advice for your flight from Chicago to San José

 
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
ORD

For a quick commute to downtown Chicago, take the CTA Blue Line train from ORD, which runs 24 hours and avoids traffic delays.

Read more about ORDby Stefanie Waldek
SJO

Arrange ground transportation in advance at SJO for a smoother exit; hotels often provide useful information and sometimes offer transport services.

Read more about SJOby Mark Chesnut
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 Chicago to San José flights

Get data-powered insights and trends into flights from Chicago to San José to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to San José
Find cheap flights to San José

Planning a trip from Chicago to San José? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to San José flight route?

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

Our data shows that the cheapest route for a return flight from Chicago to San José cost $431 and was between Chicago O'Hare Intl Airport (ORD) and San José (SJO). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $431.

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

The average price of all round-trip flights from Chicago to San José clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San José on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to San José. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago to San José?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San José, 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 Chicago to San José is July, where tickets cost $468 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $733 and $690 respectively.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $520 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San José, 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 Chicago to San José, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$116
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago O'Hare Airport to San José

When to book flights from Chicago to San José

Are your dates flexible? Find out the best times to travel from Chicago to San José 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 Chicago to San José

  • Do the airlines servicing Chicago to San Jose flights have sustainable practices?

    Passengers on flights from Chicago to San Jose release roughly 4433 lb of carbon, respectively. The eco-friendliest airlines servicing this route include Spirit Airlines, American Airlines, and Delta, which emit 39%, 38%, and 36% less carbon, respectively. American Airlines' green initiatives include implementing one-engine taxiing, Spirit Airlines features fuel-efficient aircraft, and Delta has reduced single-use plastics onboard.

  • What are the transport options from Juan Santamaria International Airport?

    Passengers arriving in San Jose from Chicago can take a bus, taxi, or shuttle to the city center. You can book a cab at the taxi kiosks near the Customs office inside SJO. The Station Wagon and Tuasa bus are across the main terminal exit and stop at Avenia 2 near Merced Park. Interbus operates shuttle buses, and you can book online or board one at the shuttle bus stop opposite the main terminal.

  • Which airlines flying from Chicago to San Jose allow pets onboard?

    Frontier and United Airlines allow small dogs and cats on board, provided you comply with their guidelines. Ensure your pet containers are roomy, ventilated, and fit under an airplane seat. Pets entering San Jose should be vaccinated and have a Veterinary Certificate for Costa Rica issued by a licensed USDA veterinarian.

  • What are the layover cities on flights from Chicago to San Jose?

    Depending on your airline, flights from Chicago to San Jose may have a connection. Spirit Airlines flights stop at Orlando International Airport (MCO) or Fort Lauderdale-Hollywood International Airport (FLL), American Airlines flights at Charlotte Douglas International Airport (CLT) or Dallas/Fort Worth International Airport (DFW), and United Airlines flights at George Bush Intercontinental Airport (IAH).

  • What is the cheapest flight from Chicago to San José?

    In the last 3 days, the lowest price for a flight from Chicago to San José was $116 for a one-way ticket and $284 for a round-trip.

  • Do I need a passport to fly between Chicago and San José?

    Yes, you’ll need a passport to travel to San José from Chicago.

  • Which airports will I be using when flying from Chicago to San José?

    Chicago is served by 2 major airports and there is only 1 main airport in San José. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at San José Juan Santamaria Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San José?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to San José flight route.

  • Which aircraft models fly most regularly from Chicago to San José?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to San José flight route.

  • Which airline alliances offer flights from Chicago to San José?

    Star Alliance is the only airline alliance operating flights between Chicago and San José.

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to San José are Southwest and Delta. With an average price for the route of $637 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 $647 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to San José?

    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 Chicago to San José.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José from Chicago 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 Chicago to San José?

    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 San José with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San José?

    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 San José from Chicago 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 Chicago to San José

  • Looking for a cheap flight? 25% of our users found flights on this route for $202 or less one-way and $493 or less round-trip.
  • You can fly from Chicago to San Jose from Chicago Midway International Airport (MDW) or O'Hare International Airport (ORD). MDW hosts low-cost airlines, so flying from the airline hub is cheaper. It is also less crowded and closer to downtown Chicago than ORD. ORD has more flight opinions to San Jose and other destinations than MDW.
  • If you are flying from Chicago to San Jose with your kids, consider booking your flight with American Airlines. The carrier is family-friendly and allows one stroller and one car seat onboard for free for parents with infants. Additionally, they offer priority boarding for ticketed customers with toddlers aged up to two.
  • Passengers with limited mobility flying from Chicago to San Jose should consider booking their flights with Frontier Airlines. The carrier allows assistive devices like wheelchairs in the cargo hold free of charge. Ensure you request special services at the time of booking.
  • Flights from Chicago to San Jose will arrive at Juan Santamaria International Airport (SJO). The airline hub is in Alajuela, roughly 12 miles west of San Jose's city center. Other towns and cities the airport serves include Santa Ana, Heredia, Escazu, and Cartago.
  • Chicago O’Hare Airport (ORD) is an American Airlines and United Airlines hub. Consider booking your flight to San Jose with the airlines for more flight options. Additionally, you can access their lounges at ORD as you await your plane.

Prefer to fly direct from Chicago to San José?

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

Direct departures

Chicago to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

San José Juan Santamaria Intl to Chicago

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to San José

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José. 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 Chicago to San José? 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 4287 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

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.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

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.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

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

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

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

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

At JFK the Security line was extremely long and few checkpoints open.

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

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

Information on your arrival and departure airports

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