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

Popular airlines from Chicago Midway Airport (MDW) to Juan Santamaria Intl. Airport (SJO)

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Frequently asked questions

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to SJO last minute?
Being spontaneous is a wonderful way to travel the world, but it's not necessarily the smartest way to land a bargain airfare. Consider booking your Midway Intl. Airport (MDW) to SJO trip in advance rather than leaving it to the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. You can unleash your spontaneous side when you arrive in SJO!
What airports do you fly into for San José from Chicago?
From Chicago, you can connect to San José via Juan Santamaria Intl. Airport (SJO), Tobias Bolanos Intl. Airport (SYQ) and Puntarenas (JAP-Chacarita). Research which terminal is right for you before you make a decision. If you pick Juan Santamaria Intl. Airport (SJO), it's roughly 16 kilometers northwest of downtown. Use the cash you save when booking your airfare with Expedia to enjoy the city's well-known sights, such as National Theater and National Park.
Can I change the date of my flight from Chicago Airport to Juan Santamaria Intl. Airport?
Make changes quickly to your MDW to SJO journey via the Expedia Trips portal. But before doing so, read through the fare rules in your itinerary to find out what the carrier will allow you to do and whether fees apply. Some carriers have a change fee per person, on top of any difference in prices. But if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also visit our Customer Service portal for more advice and to chat with our Virtual Agent.

Travel information

Origin airport
Midway Intl.
Destination airport
Juan Santamaría Intl.
Distance
3531 km

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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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