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

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

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Frequently asked questions

Is it cheaper to buy a plane ticket from SJO to Midway Airport last minute?
Booking your trip from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) last minute could save you dollars if you stumble on a real bargain. However, airfares usually don't drop in price closer to the departure date. If you procrastinate, flights could also be sold out or the best seats taken (we hope you like the middle seat!). If you'd rather play it safe, book well in advance of when you want to leave. In fact, you can find some of the biggest deals up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as offers are updated on Expedia all the time.
What airports do you fly into for Chicago from San José?
With Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to pick from, journeying from San José to Chicago is a piece of cake. The city's key hub, Midway Intl. Airport (MDW), is around 14 kilometers southwest of the downtown area. Along with ticket prices, consider things like the ease of getting from the airport and the distance to your hotel when deciding where to touch down. Get your Chicago trip off to a fun start by checking out Wrigley Field and Millennium Park.
Can I change the date of my flight from Juan Santamaria Intl. Airport to Chicago Airport?
It's easy to make changes to your SJO to Midway Airport journey yourself. Just go to the Expedia Trips portal and choose "change flight." Search for new flights and secure the one that works with your new plans. You'll get an estimate of flight change fees that may apply. You can also find your way to our Customer Service portal to chat to our Virtual Agent and quickly get answers to your questions.

Travel information

Travel information

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

Book with confidence

Book with confidence

San José to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from San José to Chicago offer the perfect respite. Not only does exploring Chicago 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 San José to Chicago 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 Chicago are only a plane trip away. Book your travel arrangements with us today!

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

San José to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia