S$299 Cheap Flights from Chicago to San José

View S$299 flight on Sat, 23 Aug, 2025Opens 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 S$299 for one-way flights and S$596 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 12 Aug - Fri, 22 Aug
ORD
Chicago
SJO
San José
S$596 Return, found 4 days ago
S$596
Return
found 4 days ago
Select American Airlines flight, departing Tue, 12 Aug from Chicago to San José, returning Fri, 22 Aug, priced at S$596 found 4 days ago
American Airlines
Tue, 12 Aug - Fri, 22 Aug
ORD
Chicago
SJO
San José
S$604 Return, found 4 days ago
S$604
Return
found 4 days ago
Select American Airlines flight, departing Tue, 12 Aug from Chicago to San José, returning Fri, 22 Aug, priced at S$604 found 4 days ago
United
Tue, 12 Aug - Fri, 22 Aug
ORD
Chicago
SJO
San José
S$621 Return, found 4 days ago
S$621
Return
found 4 days ago
Select United flight, departing Tue, 12 Aug from Chicago to San José, returning Fri, 22 Aug, priced at S$621 found 4 days ago
United
Tue, 12 Aug - Fri, 22 Aug
ORD
Chicago
SJO
San José
S$629 Return, found 4 days ago
S$629
Return
found 4 days ago
Select United flight, departing Tue, 12 Aug from Chicago to San José, returning Fri, 22 Aug, priced at S$629 found 4 days ago
American Airlines
Tue, 12 Aug - Fri, 22 Aug
ORD
Chicago
SJO
San José
S$651 Return, found 4 days ago
S$651
Return
found 4 days ago
Select American Airlines flight, departing Tue, 12 Aug from Chicago to San José, returning Fri, 22 Aug, priced at S$651 found 4 days ago
American Airlines
Sun, 24 Aug - Sun, 31 Aug
ORD
Chicago
SJO
San José
S$652 Return, found 5 days ago
S$652
Return
found 5 days ago
Select American Airlines flight, departing Sun, 24 Aug from Chicago to San José, returning Sun, 31 Aug, priced at S$652 found 5 days ago
American Airlines
Sun, 24 Aug - Sun, 31 Aug
ORD
Chicago
SJO
San José
S$659 Return, found 5 days ago
S$659
Return
found 5 days ago
Select American Airlines flight, departing Sun, 24 Aug from Chicago to San José, returning Sun, 31 Aug, priced at S$659 found 5 days ago
Copa
Sun, 24 Aug - Sun, 31 Aug
ORD
Chicago
SJO
San José
S$699 Return, found 5 days ago
S$699
Return
found 5 days ago
Select Copa flight, departing Sun, 24 Aug from Chicago to San José, returning Sun, 31 Aug, priced at S$699 found 5 days ago
avianca
Sun, 24 Aug - Sun, 31 Aug
ORD
Chicago
SJO
San José
S$733 Return, found 5 days ago
S$733
Return
found 5 days ago
Select avianca flight, departing Sun, 24 Aug from Chicago to San José, returning Sun, 31 Aug, priced at S$733 found 5 days ago
Delta
Mon, 1 Jun - Mon, 8 Jun
ORD
Chicago
SJO
San José
S$1,181 Return, found 23 hours ago
S$1,181
Return
found 23 hours ago
Select Delta flight, departing Mon, 1 Jun from Chicago to San José, returning Mon, 8 Jun, priced at S$1,181 found 23 hours ago

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

August is typically the cheapest month to fly

From S$341 - S$531 per traveller.

Graph displaying average flight prices per month

Chicago to San José route information
Origin airport
O'Hare Intl.
Destination airport
Juan Santamaría Intl.
Airlines serving
Aeromexico, Air Canada, American Airlines, Copa, Delta, United, avianca
Return price
S$596
Distance
3553 km
Average flight time
5 hours 9 mins

Perfect flights from Chicago to San José

Your Journey from Chicago to San José

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San José 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 Copa, American Airlines, United, Air Canada, avianca, Delta. Our selection of flights from O'Hare Intl. to Juan Santamaría Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San José Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Juan Santamaría Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$299 and roundtrip prices from S$596*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San José 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 San José

Picture yourself stepping off the plane in San José 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 Chicago to San José 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 Chicago to San José.
 

Beyond the Flight – Exploring San José

With Expedia, your adventure extends beyond the flight. Explore San José 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 Chicago to San José 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 Chicago to San José 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 ORD to Juan Santamaria Intl. Airport?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip flight from ORD to SJO was S$596. Fares this cheap don't hang around, so make sure you book yours ASAP. 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?
When it comes to cancellation fees, each airline has its own terms and conditions. If you decide to cancel your escape, visit our Customer Service Portal.
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 (SJO) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Juan Santamaria Intl. Airport (SJO)?
Around 3,600 kilometres separates Chicago and San Jose, so pack something to help you fill in a couple of hours. That action-packed novel you haven't had time to start will be just the ticket.
Which airlines fly direct from O'Hare Airport to Juan Santamaria Intl. Airport (SJO)?
Direct flights aren't available, so you'll have to make at least one stop between O'Hare Intl. Airport (ORD) and Juan Santamaria Intl. Airport. Take advantage of the layover time to stretch your legs and grab a bite to eat.
Are O'Hare Airport to Juan Santamaria Intl. Airport (SJO) flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes nab a bargain, with some of the cheapest airfares from ORD to Juan Santamaria Intl. Airport (SJO) showing up a few weeks prior to the departure date. If you'd rather book ahead of time, Expedia compares and updates the best flight deals regularly --- as early as 12 months in advance in some cases. It does depend on the carrier though, as not every airline advertises prices so far in advance.

Explore a world of travel with Expedia

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