S$472 Cheap Flights from San José to Chicago

View S$472 flight on Fri, 20 Feb, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at S$472 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

October is typically the cheapest month to fly

From S$220 - S$499 per traveller.
San José to Chicago route information
Origin airport
Juan Santamaría Intl.
Destination airport
O'Hare Intl.
Distance
3553 km
Average flight time
6 hours 9 mins

Perfect flights from San José to Chicago

Your Journey from San José to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San José to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, Copa, American Airlines, avianca, United, Aeromexico. Our selection of flights from Juan Santamaría Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 9 airlines, you're bound to find the perfect flight.
 

Maximizing Value with San José to Chicago Flights

Experience the joy of finding cheap flights from Juan Santamaría Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$472 and roundtrip prices *.
 

Pre-Flight Essentials

Ensure a smooth journey from San José to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your San José to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from San José to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from San José to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from San José to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Juan Santamaria Intl. Airport to O'Hare Airport?
Start packing your suitcase, because round-trip journeys from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD) start from . That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book now to get the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Juan Santamaria Intl. Airport (SJO) to O'Hare Airport 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 Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from SJO to O'Hare Intl. Airport (ORD)?
The flight distance between SJO (SJO) and ORD (ORD) is 3,600 kilometres. Work your way through your travel song playlist or bury your nose in a book and the journey will zip on by.
Which airlines fly direct from SJO to ORD?
If you want to travel straight from Juan Santamaria Intl. Airport to O'Hare Airport, you'll need to book a flight with one or more stops. Unfortunately, there are no airlines that fly directly on this route.
Are Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from Juan Santamaria Intl. Airport (SJO) to ORD can be hit-or-miss. You might be lucky and score a bargain, but then again, you could miss out entirely! If you'd rather start your trip planning early on, Expedia compares flight deals up to a year in advance. Just remember that not all airlines list their prices that far in advance. Our suggestion? Check back often as updates are made regularly.

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