S$295 Cheap Flights from Chicago to San José

View S$295 flight on Sun, 8 Mar, 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 S$295 for one-way flights and S$633 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 7 Mar - Sat, 14 Mar
ORD
Chicago
SJO
San José
S$633 Return, found 1 hour ago
S$633
Return
found 1 hour ago
Select Delta flight, departing Sat, 7 Mar from Chicago to San José, returning Sat, 14 Mar, priced at S$633 found 1 hour ago
Copa
Sun, 8 Mar - Sun, 15 Mar
ORD
Chicago
SJO
San José
S$689 Return, just found
S$689
Return
just found
Select Copa flight, departing Sun, 8 Mar from Chicago to San José, returning Sun, 15 Mar, priced at S$689 just found
Copa
Sun, 8 Mar - Fri, 13 Mar
ORD
Chicago
SJO
San José
S$708 Return, found 23 hours ago
S$708
Return
found 23 hours ago
Select Copa flight, departing Sun, 8 Mar from Chicago to San José, returning Fri, 13 Mar, priced at S$708 found 23 hours ago
Copa
Sat, 7 Mar - Sun, 15 Mar
ORD
Chicago
SJO
San José
S$743 Return, just found
S$743
Return
just found
Select Copa flight, departing Sat, 7 Mar from Chicago to San José, returning Sun, 15 Mar, priced at S$743 just found
Delta
Sat, 7 Mar - Sat, 14 Mar
ORD
Chicago
SJO
San José
S$767 Return, found 1 hour ago
S$767
Return
found 1 hour ago
Select Delta flight, departing Sat, 7 Mar from Chicago to San José, returning Sat, 14 Mar, priced at S$767 found 1 hour ago
American Airlines
Sun, 8 Mar - Fri, 13 Mar
ORD
Chicago
SJO
San José
S$772 Return, found 23 hours ago
S$772
Return
found 23 hours ago
Select American Airlines flight, departing Sun, 8 Mar from Chicago to San José, returning Fri, 13 Mar, priced at S$772 found 23 hours ago
Copa
Sun, 8 Mar - Sun, 15 Mar
ORD
Chicago
SJO
San José
S$781 Return, just found
S$781
Return
just found
Select Copa flight, departing Sun, 8 Mar from Chicago to San José, returning Sun, 15 Mar, priced at S$781 just found
United
Sat, 7 Mar - Sat, 14 Mar
ORD
Chicago
SJO
San José
S$789 Return, found 1 hour ago
S$789
Return
found 1 hour ago
Select United flight, departing Sat, 7 Mar from Chicago to San José, returning Sat, 14 Mar, priced at S$789 found 1 hour ago
United
Sat, 7 Mar - Sat, 14 Mar
ORD
Chicago
SJO
San José
S$789 Return, found 1 hour ago
S$789
Return
found 1 hour ago
Select United flight, departing Sat, 7 Mar from Chicago to San José, returning Sat, 14 Mar, priced at S$789 found 1 hour ago
Air Canada
Sun, 8 Mar - Fri, 13 Mar
ORD
Chicago
SJO
San José
S$799 Return, found 23 hours ago
S$799
Return
found 23 hours ago
Select Air Canada flight, departing Sun, 8 Mar from Chicago to San José, returning Fri, 13 Mar, priced at S$799 found 23 hours ago

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

October is typically the cheapest month to fly

From S$240 - S$536 per traveller.

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$633. 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.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Juan Santamaría Intl.
Airlines serving
Air Canada, American Airlines, Copa, Delta, United, avianca
Return price
S$632
Distance
3553 km
Average flight time
5 hours 9 mins

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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 Air Canada, Delta, avianca, Copa, American Airlines, United. 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$295 and roundtrip prices from S$633*.
 

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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

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to San José

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