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Good to Know - Flights from Chicago to San Jose

Good Deal:
$ 271.93
or less (round trip)

Cheapest Day of the Month to Book Flights



Top Tips for Finding Cheap Flights from Chicago to San Jose

Looking for cheap airfare from Chicago to San Jose? 25% of our users found round-trip tickets to San Jose for the following price or less: $ 271.93 Book at least 4 weeks before departure in order to get a below-average price. Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago to San Jose flight deals.

FAQs - Booking from Chicago to San Jose flights

What is the cheapest flight Chicago to San Jose?:
The cheapest flight Chicago to San Jose found on flyus.com in the last 72 hours was $271.93 round-trip.
 
 

Find cheap flights from Chicago to San Jose and book discounted airfare from different cities all over the United States. Explore airline ticket deals on flight routes all over the World! At Flyus, we take pride in helping you discover and book the best flight deals for your next trip at the cheapest price. We make booking flights from different departures easy and provide you with peace of mind with our Best Purchase Guarantee.

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Cheapest Flights
from Chicago, United States (ORD) to:

  • San Jose, Costa Rica (SJO)
    Feb 22, 25 - Feb 26, 25
    $271.93
    Search

  • San Jose, Costa Rica (SJO)
    Jan 21, 25 - Jan 29, 25
    $271.93
    Search

  • San Jose, Costa Rica (SJO)
    Jan 23, 25 - Jan 28, 25
    $281.93
    Search

  • San Jose, Costa Rica (SJO)
    Feb 03, 25 - Feb 08, 25
    $319.93
    Search

  • San Jose, Costa Rica (SJO)
    Feb 06, 25 - Feb 13, 25
    $319.93
    Search