CHI - SJO

$73 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 9/7. 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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Flight 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

Sat, Nov 1 - Tue, Nov 4
Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:35 pm - 1:03 amSJO-ORD
11h 28m1 stop
$285Spirit Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:35 pm - 7:16 pmSJO-ORD
29h 41m2 stops
$287Spirit Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 17
 Logo
4:30 pm - 1:20 amORD-SJO
8h 50m1 stop
 Logo
1:19 pm - 9:00 pmSJO-ORD
7h 41m1 stop
Sat, Sep 20 - Wed, Sep 24
 Logo
10:27 am - 10:40 pmORD-SJO
13h 13m1 stop
 Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:15 am - 12:34 pmMDW-SJO
7h 19m1 stop
Frontier Logo
1:49 pm - 11:25 pmSJO-MDW
8h 36m1 stop
$364Frontier
Find Deal
Thu, Nov 6 - Wed, Nov 12
Delta Logo
6:00 am - 12:50 pmMDW-SJO
6h 50m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$394Delta
Find Deal
Wed, Nov 19 - Tue, Nov 25
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
Delta Logo
7:00 am - 9:44 pmSJO-MDW
14h 44m1 stop
$398Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
6:15 am - 12:45 pmMDW-SJO
7h 30m1 stop
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$427Southwest
Find Deal
Mon, Oct 20 - Fri, Oct 24
Southwest Logo
8:05 pm - 12:05 pmMDW-SJO
17h 00m2 stops
Southwest Logo
1:30 pm - 12:05 amSJO-MDW
9h 35m2 stops
$431Southwest
Find Deal
Fri, Oct 17 - Sat, Oct 25
Frontier Logo
6:24 pm - 12:34 pmMDW-SJO
19h 10m2 stops
Frontier Logo
1:49 pm - 11:25 pmSJO-MDW
8h 36m1 stop
$443Frontier
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.
Airlines
United Airlines

Opt for United Polaris for lie-flat seats and aisle access on long-haul flights.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for better connectivity.

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.

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 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
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
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
Booking Insights

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.

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

What is the cheapest Chicago to San José flight route?

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

The cheapest return flight from Chicago to San José costs $461 on the route between Chicago O'Hare Intl Airport (ORD) and San José (SJO). It is also the most popular route.

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 September, where tickets cost $445 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $732 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 $804 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, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$73
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 18% 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 $73 for a one-way ticket and $285 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.

  • What is the most popular layover when flying to San José from Chicago?

    Fort Lauderdale is the most popular layover city among KAYAK users traveling from Chicago to San José.

  • 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 $628 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 $664 and an overall rating of 7.9.

  • 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 $268 or less one-way and $563 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.

Reviews of the 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 4246 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

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

Great experience with a crew always thinking in the passenger

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

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

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.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

I liked the check in procedure. The luggage charges and overweight cost can be better.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

We liked the woman who worked our gate and waited with us for our plane. We changed gates 3 times. Our flight was supposed to leave at 11:28am. We actually left after 5pm. It was not a good situation. This delay cost us a lot of money.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

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

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