Cheap Flights from San Jose (SJI) to Chicago (ORD)

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Flight from San Jose to Chicago route information
Origin airport
San Jose
Destination airport
O'Hare Intl.
Distance
13208 km

Compare flights from San Jose to Chicago easily and book in confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from San Jose to Chicago. Operating between them flights per day, airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from San Jose to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from San Jose (SJI) to O'Hare Intl. (ORD) 

The easiest way to view the best deals on flights from San Jose to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from San Jose to O'Hare Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near San Jose and Chicago
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your San Jose to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from San Jose to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from SJI to O'Hare Intl. Airport (ORD)?
Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Norman Y. Mineta San Jose Intl. Airport and ORD start from . Make your booking today to get the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Norman Y. Mineta San Jose Intl. Airport to O'Hare Airport?
This can differ between airlines, as each has its own set of terms and conditions. Visit the Customer Service Portal, where there are simple instructions on how to cancel online.
How do I find cheap flights from Norman Y. Mineta San Jose Intl. Airport to O'Hare Airport 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 SJI to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from SJI to O'Hare Airport?
San Jose to Chicago is around 13,300 kilometres, so be prepared to spend a while in the air. Don’t forget to pack all the essentials, from your toothbrush to your hairbrush. Take a couple of snacks to munch on throughout your flight too.
Which airlines fly direct from San Jose Airport (SJI) to O'Hare Intl. Airport (ORD)?
If you want to fly straight from Norman Y. Mineta San Jose Intl. Airport to O’Hare Intl. Airport (ORD), you’ll have to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are San Jose Airport (SJI) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally score a bargain, with some super cheap airfares from San Jose Airport (SJI) to ORD surfacing a few weeks before the date of departure. If you’d rather book ahead, Expedia compares and updates all the best flight deals regularly — as early as 12 months in advance in some cases. It depends on the carrier though, as not all airlines advertise prices that far in advance.
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