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

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

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Frequently asked questions

How long does it take to fly from O'Hare Airport to Juan Santamaria Intl. Airport?
Purchase a ticket with United Airlines and you can expect to be in the air for around 5 hours and 14 minutes. This top airline operates a direct flight that leaves at 7:41AM from O'Hare Airport and reaches Juan Santamaria Intl. Airport at 11:55AM. Expedia has some amazing flight deals, so take a look at what's available on this route today.
Is it cheaper to buy a plane ticket from ORD to SJO last minute?
When it's time to book your flights, it's always better to be prepared. While it's possible to pick up a last-minute deal on an O'Hare Airport to SJO flight, prices usually don't get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international trips it's three to four months.
What airline has the least delays from O'Hare Airport to Juan Santamaria Intl. Airport?
Journey with United Airlines from O'Hare Intl. Airport (ORD) to SJO and land at the time listed on your boarding card. This carrier leads the way on this route, with an on-time rate of 100%. If there is a delay to your flight, the free Expedia App is the ideal way to stay in the loop. Our handy app will give you real-time trip alerts, from flight delays to gate changes and baggage carousel numbers.
What airports do you fly into for San José from Chicago?
Juan Santamaria Intl. Airport (SJO), Tobias Bolanos Intl. Airport (SYQ) and Puntarenas (JAP-Chacarita) are your choices when taking off from Chicago to San José. Approximately 16 kilometers northwest of the center of San José, Juan Santamaria Intl. Airport (SJO) is the city's major hub. Think about things such as flight departure and arrival times and the distance to your hotel before you select an airport. National Theater and National Park are two awesome attractions to check out when you arrive at your destination.
What are the most popular departure times for flights from O'Hare Airport to Juan Santamaria Intl. Airport (SJO)?
For United Airlines flights from ORD to Juan Santamaria Intl. Airport (SJO), the busiest period is between 7:00 AM - 8:00 AM. If you want to avoid holdups, head out in the morning. This gives you a better chance to dodge air traffic that builds up in the skyways later in the day.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to SJO?
It's a snap to make changes to your O'Hare Intl. Airport (ORD) to Juan Santamaria Intl. Airport (SJO) trip yourself. Simply go to the Expedia Trips portal and hit "change flight." Look for new flights and secure the one that fits your plans. You'll see an estimate of any flight change costs. You can also head to our Customer Service portal to connect with our Virtual Agent and get answers to all your questions.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Juan Santamaría Intl.
Distance
3553 km

Book with confidence

Book with confidence

Chicago to San José Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to San José offer the perfect respite. Not only does exploring San José provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to San José may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of San José are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to San José more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to San José is now!

Chicago to San José Flights

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Explore a world of travel with Expedia