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

Pick up great flights from Chicago to San Jose

With Expedia, you have your pick of 2 flights a day with 12 airlines covering flights from Chicago to San Jose. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to San Jose that take around 4 hours.

Find cheap flights from Chicago to San Jose

From the great flight deals with prices currently ranging from AU$775 to AU$953, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to San Jose around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to San Jose is normally in December.

Reasons to book your flight from Chicago to San Jose with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to San Jose across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to San Jose right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.