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Book Flights from Chicago to San Jose will help you to find the best deals on flights from Chicago to San Jose. With our search technology, effortlessly searching flight routes across hundreds of airlines has never been easier or more convenient. With, we aim to make it simple and quick to search, select and save on the flights that best suit your needs and budget.

No matter if you are traveling for business or pleasure, we offer a wide range of deals from business class discounts to last minute flight deals to destinations like San Jose. Whether you are planning ahead or looking for last minute tickets, CheapOair has the right flights at the right price. After booking your ticket, explore this page to view blog posts about this destination, learn more about hotels near SJC and read reviews from others who booked their flights with

Frequently Asked Questions - Chicago to San Jose Flights

  • When does the first flight of the day depart from CHI?

    9:55AM Southwest Airlines Flight #3211

  • When does the last flight depart to SJC?

    8:19PM Southwest Airlines Flight #3766

  • What is the travel distance between Chicago and San Jose?

    1,841 miles

  • How many weekly flights are there between CHI to SJC?

    There are 7 weekly flights between CHI and SJC.

  • Which is the busiest day in terms of passengers traffic between CHI to SJC?


  • Which is the nearest airport to San Jose, California?

    San Jose International Airport

  • Which is the nearest airport to Chicago, Illinois?

    Midway International Airport