￥27,770 Cheap Flights from San José (SJO) to Chicago (ORD)

View ￥27,770 flight on Thu, Dec 18, 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 ￥27,770 for one-way flights and ￥55,460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Copa
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥55,460 Roundtrip, found 1 day ago
￥55,460
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥55,460 found 1 day ago
Copa
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥57,780 Roundtrip, found 1 day ago
￥57,780
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥57,780 found 1 day ago
Copa
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥66,110 Roundtrip, found 1 day ago
￥66,110
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥66,110 found 1 day ago
Copa
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥68,530 Roundtrip, found 1 day ago
￥68,530
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥68,530 found 1 day ago
United
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥69,190 Roundtrip, found 1 day ago
￥69,190
Roundtrip
found 1 day ago
Select United flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥69,190 found 1 day ago
Delta
Thu, Dec 18 - Tue, Jan 6
SJO
San José
ORD
Chicago
￥69,470 Roundtrip, found 6 days ago
￥69,470
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 18 from San José to Chicago, returning Tue, Jan 6, priced at ￥69,470 found 6 days ago
Delta
Thu, Dec 18 - Tue, Jan 6
SJO
San José
ORD
Chicago
￥70,100 Roundtrip, found 6 days ago
￥70,100
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 18 from San José to Chicago, returning Tue, Jan 6, priced at ￥70,100 found 6 days ago
Delta
Thu, Dec 18 - Tue, Jan 6
SJO
San José
ORD
Chicago
￥70,300 Roundtrip, found 6 days ago
￥70,300
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 18 from San José to Chicago, returning Tue, Jan 6, priced at ￥70,300 found 6 days ago
American Airlines
Thu, Dec 18 - Tue, Jan 6
SJO
San José
ORD
Chicago
￥72,360 Roundtrip, found 6 days ago
￥72,360
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Dec 18 from San José to Chicago, returning Tue, Jan 6, priced at ￥72,360 found 6 days ago
Air Canada
Mon, Oct 27 - Sat, Nov 1
SJO
San José
ORD
Chicago
￥76,830 Roundtrip, found 1 day ago
￥76,830
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Oct 27 from San José to Chicago, returning Sat, Nov 1, priced at ￥76,830 found 1 day ago

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

September is typically the cheapest month to fly

From ￥25,515 - ￥100,895 per traveler.

Frequently asked questions

How much is a flight from Juan Santamaria Intl. Airport to O'Hare Airport?
The lowest price advertised for a round-trip journey between SJO and ORD is ￥55,460. But you better get a move on. This figure is taken from fares offered within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from SJO to O'Hare Intl. Airport (ORD)?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the simple instructions on our Customer Service Portal.
How do I find cheap flights from Juan Santamaria Intl. Airport to O'Hare Intl. Airport (ORD) 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 Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
To comfortably pass the 9 hours and 49 minutes flight time between SJO and O'Hare Intl. Airport (ORD), it's wise to prepare before you leave home. A smartphone loaded up with your favorite TV series is a fantastic start.
How far is the flight from SJO to ORD?
The flight distance from Juan Santamaria Intl. Airport (SJO) to ORD is 3,600 kilometers. Bring along a drink, a few snacks and a good movie. Keep yourself entertained and the hours will fly by.
Which airlines fly direct from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
At present, no airlines offer direct flights from Juan Santamaria Intl. Airport to ORD. You'll have to book a flight with one or more stops. To get the best price and connections, lock in your fare well in advance.
Are SJO to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Juan Santamaria Intl. Airport to ORD can be hit-or-miss. You may be able to find a bargain, but you could also miss out completely! If you'd rather start planning your trip early on, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines issue their prices so far in advance. Our top tip? Check back often as prices are updated regularly.

Travel information

Travel information

Origin airport
Juan Santamaría Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, Copa, Delta, United, avianca
Roundtrip price
￥55,460
Distance
3553 km

Book with confidence

Book with confidence

San José to Chicago 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 San José 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 Chicago.

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 SJO to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind San José 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 ORD 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.

San José to Chicago Flights

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