Cheap Flights from Chicago (MDW) to San Jose (SJC)

Popular airlines from Chicago Midway Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)

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Find the cheapest month to fly from Chicago (MDW) to San Jose (SJC)

October is typically the cheapest month to fly

From £103 - £451 per traveller.

Graph displaying average flight prices per month

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Flight from Chicago to San Jose route information
Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Distance
2933 km

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

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to San Jose. Operating between them 1 flights per day, airlines cover the route. And Southwest Airlines fly direct, getting you to Norman Y. Mineta San Jose Intl. in just 4hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Midway Intl. to Norman Y. Mineta San Jose 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 Midway Intl. (MDW) to Norman Y. Mineta San Jose Intl. (SJC)

The easiest way to view the best deals on flights from Chicago to San Jose 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 Midway Intl. to Norman Y. Mineta San Jose 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 Chicago and San Jose
  • 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 Chicago to San Jose flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Midway Intl. to Norman Y. Mineta San Jose 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 MDW to San Jose Intl. Airport?
Round-trip journeys from Midway Airport to Norman Y. Mineta San Jose Intl. Airport (SJC) start from . This price is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to San Jose Intl. Airport?
Most flights can be cancelled online, but every air carrier has different terms and conditions. If you do have to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Norman Y. Mineta San Jose Intl. Airport (SJC) 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 MDW to SJC flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Midway Airport to San Jose Intl. Airport?
It takes approximately 6 hours and 18 minutes to fly from MDW (MDW) to San Jose Intl. Airport (SJC). But with some movies and a few interesting magazines, the time will go by quicker.
How far is the flight from Chicago Airport to San Jose Intl. Airport?
It's around 3,000 kilometres between Chicago and San Jose, so you'll be in your seat for a while. Keep yourself occupied by packing things like playing cards (if you're travelling with friends) or a thrilling novel.
Which airlines fly direct from MDW to San Jose Intl. Airport?
Check out the airfares with Southwest Airlines (WN) if you want to fly directly from MDW to San Jose Intl. Airport. This top airline offers 30 flights monthly, so you're sure to find one that fits your schedule.
Are Midway Airport to San Jose Intl. Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a fantastic last-minute deal from Chicago Airport to SJC, but it's also possible to miss out entirely! As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you see a bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can be certain you're always getting the latest offers.

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San Jose Airports

San Francisco

Chicago Airports

Chicago

O'Hare Intl. to San Jose
£236.10
*Available to Expedia members.