Cheap flights from Chicago to San Jose
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Check our current prices for flights from Chicago to San Jose. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to San Jose, you will need to run a search below.
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Cheap San Jose airfares from $1236/RT are provided by Cheapoair.com. Outbound flight is leaving on 12/23/2025, 01:13 am from Chicago O`hare (ORD) airport and arrives at San Jose Santamaria (SJO) at 11:53 am. The flight time is 10 hours and 40 minutes. The Returning flight departes on 01/04/2026, 05:45 am (other return dates are also available). Date posted: 03 Feb 2025
Price evolution for flights From Chicago To San Jose
Recent Deals on Flights from Chicago to San Jose:Roundtrip / Oneway
- $1236
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Jose, CR (SJO) 12/23/2025 01:13 am San Jose, CR (SJO) Chicago, IL (ORD) 01/04/2026 05:45 am - $1446 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Jose, CR (SJO) 12/23/2025 01:55 am San Jose, CR (SJO) Chicago, IL (ORD) 01/04/2026 05:45 am - We are sorry but currently there are no oneway offers for flights from Chicago to San Jose.
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Know what to do when flying to San Jose?
San Jose Travel Guide Enjoy your vacations in San Jose - Overview San Jose, the largest city of Silicon Valley is about a 50 miles south of the South Francisco is linked with cutting-edge technology and innovation. The city of San José has faced quite a hit even [...]San Jose History San José in Costa Rica has a fascinating history. It is currently the capital of Costa Rica but it was not the original capital. It was first a small pueblo that was founded in 1738. Cartago was the original capital of Costa Rica. Many [...]
San Jose Sightseeing If you are going to San Jose, Costa Rica there are a few places that you will have to go to. San Jose is rather small but it does not lack entertainment. These destinations will teach you about local culture, its history and dedication to [...]
San Jose Nightlife In San Jose, Costa Rica, there is an active nightlife. No matter what you like to do, San Jose has something for you. If you prefer to have a relaxed night out on the town, there are various bars that are low key and have a tranquil, [...]
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