￥36,750 Cheap Flights from Chicago (ORD) to San José (SJO)

View ￥36,750 flight on Sat, Jan 31, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Juan Santamaria Intl. Airport (SJO)

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

Prices were available within the past 7 days and start at ￥36,750 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Chicago (ORD) to San José (SJO)

October is typically the cheapest month to fly

From ￥28,213 - ￥44,897 per traveler.

Frequently asked questions

How much is a flight from O'Hare Airport to Juan Santamaria Intl. Airport?
If you're traveling between O'Hare Intl. Airport (ORD) and Juan Santamaria Intl. Airport, round-trip journeys start from . This price is based on airfares listed within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to SJO?
We understand that life can throw the odd curveball, so we've made it as hassle-free as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from ORD to SJO that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to Juan Santamaria Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from ORD to Juan Santamaria Intl. Airport (SJO)?
The flight time from O'Hare Airport to Juan Santamaria Intl. Airport is about 9 hours and 50 minutes. It's is no small journey, so fill your hand luggage with plenty to keep you entertained.
How far is the flight from ORD to Juan Santamaria Intl. Airport?
Around 3,600 kilometers separates Chicago and San José, so pack something to help you while away a couple of hours. That thrilling novel you haven't had time to start will do the trick.
Which airlines fly direct from ORD to SJO?
Flying directly between ORD and SJO isn't possible right now. However, you'll still be able to book a flight to San José with at least one stop.
Are O'Hare Intl. Airport (ORD) to Juan Santamaria Intl. Airport (SJO) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from O'Hare Airport to Juan Santamaria Intl. Airport at the last minute could be your ticket to an awesome deal. However, it might cost you a whole lot more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back often as deals are updated all the time on Expedia.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Juan Santamaría Intl.
Distance
3553 km
Average flight time
5 hours 8 mins

Book with confidence

Chicago to San José Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring San José.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with ORD to SJO flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to SJO with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Chicago to San José Flights

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