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  1. Flights
  2. Costa Rica
  3. San Jose
  4. Chicago - San Jose

Flights Chicago - San Jose - eDreams Canada

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Explore the best deals

Discover the cheapest flights from Chicago to San Jose
Filter by
Sun, Nov 15 - Fri, Nov 20
CM
CMDirect
CHI - SJO
CM
CMDirect
SJO - CHI
569$
533$
Prime price per passenger
Fri, Nov 27 - Sat, Dec 5
AA
AADirect
CHI - SJO
AA
AADirect
SJO - CHI
618$
589$
Prime price per passenger
Wed, Dec 9 - Sun, Dec 13
AA
AADirect
CHI - SJO
AA
AADirect
SJO - CHI
671$
647$
Prime price per passenger
Mon, Dec 21 - Sun, Dec 27
AA
AADirect
CHI - SJO
AA
AADirect
SJO - CHI
865$
852$
Prime price per passenger
Wed, Dec 30
AA
AADirect
CHI - SJO
458$
438$
Prime price per passenger
Thu, Nov 26
AC
ACDirect
CHI - SJO
510$
465$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to San Jose

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the beginning of November. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
Filter by
week: Nov 2 - Nov 8
Flights from just $381
$381
$438
$384
$918
$580
NovemberDecember
Distance: 3,564 km
Chicago airports
San Jose airports
Juan Santamaria International Airport (SJO)How far from city centre: 1 km

FAQs about flights between Chicago and San Jose

What is the usual price for a ticket from Chicago to San Jose?
The average ticket price for a flight from Chicago to San Jose is about $558. This can change depending on travel dates, demand, and how far in advance the flight is booked.
What’s the best way to find cheap flights from Chicago to San Jose on eDreams?
The lowest current fare from Chicago to San Jose is $ 438. Thanks to our system, we identify the best options across different airlines and itineraries to combine value and flexibility for your journey.
When is the right time to book flights from Chicago to San Jose?
The top months when travelers usually book a ticket from Chicago to San Jose are October, September and August, based on search trends from our platform.
When is the best season to travel from Chicago to San Jose?
The best moment to travel to San Jose from Chicago depends on whether you prioritize price, climate, or avoiding crowds. The busiest travel month is December, followed by January and March. To avoid peak travel, consider going in September, August or July, when demand is lower for the Chicago - San Jose route.
How many hours is the flight from Chicago to San Jose?
Flying between Chicago and San Jose generally takes about 7 h and 5 m, for a distance of approximately 3,564.13 km. Times may vary depending on whether you choose a direct flight or one with layovers.
Which airlines operate routes between Chicago and San Jose?

Copa Airlines

  • Avianca
  • Frontier Airlines

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