S$266 Cheap Flights from San José to Chicago

View S$266 flight on Fri, 22 Aug, 2025Opens 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$266 for one-way flights and S$460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$460 Return, found 6 days ago
S$460
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$460 found 6 days ago
avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$477 Return, found 6 days ago
S$477
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$477 found 6 days ago
avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$585 Return, found 6 days ago
S$585
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$585 found 6 days ago
avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$590 Return, found 6 days ago
S$590
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$590 found 6 days ago
avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$597 Return, found 6 days ago
S$597
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$597 found 6 days ago
avianca
Fri, 22 Aug - Fri, 29 Aug
SJO
San José
ORD
Chicago
S$602 Return, found 6 days ago
S$602
Return
found 6 days ago
Select avianca flight, departing Fri, 22 Aug from San José to Chicago, returning Fri, 29 Aug, priced at S$602 found 6 days ago
American Airlines
Thu, 28 Aug - Thu, 4 Sep
SJO
San José
ORD
Chicago
S$655 Return, found 15 hours ago
S$655
Return
found 15 hours ago
Select American Airlines flight, departing Thu, 28 Aug from San José to Chicago, returning Thu, 4 Sep, priced at S$655 found 15 hours ago
United
Wed, 27 Aug - Wed, 3 Sep
SJO
San José
ORD
Chicago
S$695 Return, found 1 day ago
S$695
Return
found 1 day ago
Select United flight, departing Wed, 27 Aug from San José to Chicago, returning Wed, 3 Sep, priced at S$695 found 1 day ago
Copa
Thu, 28 Aug - Thu, 4 Sep
SJO
San José
ORD
Chicago
S$721 Return, found 15 hours ago
S$721
Return
found 15 hours ago
Select Copa flight, departing Thu, 28 Aug from San José to Chicago, returning Thu, 4 Sep, priced at S$721 found 15 hours ago
Aeromexico
Thu, 28 Aug - Thu, 4 Sep
SJO
San José
ORD
Chicago
S$1,052 Return, found 15 hours ago
S$1,052
Return
found 15 hours ago
Select Aeromexico flight, departing Thu, 28 Aug from San José to Chicago, returning Thu, 4 Sep, priced at S$1,052 found 15 hours ago

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

May is typically the cheapest month to fly

From S$341 - S$579 per traveller.

Graph displaying average flight prices per month

San José to Chicago route information
Origin airport
Juan Santamaría Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, American Airlines, Copa, United, avianca
Return price
S$460
Distance
3553 km
Average flight time
7 hours 37 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 avianca, American Airlines, Copa, 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 20 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$266 and roundtrip prices from S$460*.
 

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 S$460. 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.

Explore a world of travel with Expedia

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