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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to San José (SYQ-Tobías Bolaños Intl.)

Alternative airports near San José

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Juan Santamaria Intl. SJO. Cheapest option available. Average driving time to city center is 20 minutes. Flights from $267
SJO
Juan Santamaria Intl.
Cheapest
Average driving time to city center20 min
Flights from $267

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ) cost?
Grab a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ)?
Planning your getaway for is a great way to save, as it's the cheapest month for flights between ORD and SYQ. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from ORD to SYQ. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ)?
Nonstop flights from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to SYQ?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change based on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ)?
To land at Tobias Bolanos Intl. Airport (SYQ) without delays, book a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for San José from O'Hare Intl. Airport (ORD)?
If you're boarding a direct flight from O'Hare Intl. Airport (ORD) to San José, Juan Santamaria Intl. Airport (SJO) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ) last-minute?
Waiting until just before your departure to book a ticket from ORD to SYQ often results in higher prices. While you may find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book an ORD to SYQ flight and hotel package?
You can save money by securing an ORD to SYQ flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After choosing your ideal accommodations and flights, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Tobias Bolanos Intl. Airport (SYQ)?
If you booked your ORD to SYQ flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Tobías Bolaños Intl.
Distance
2223 mi

Book with confidence

Chicago to San José Flights

The cheapest times to fly from Chicago to San José

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San José are during the month of . You can find some of the cheapest flights from Chicago to San José with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San José

Sunday is one of the best days to book for cheap flights from Chicago to San José: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San José

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San José in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San José flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San José airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to San José Flights

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*Available to One Key members.