Cheap flights from Chicago to San Jose
Travel > Central America > Costa Rica > Chicago to San Jose flights
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.
Search and Compare cheap Flights
Book your flight now with Cheapoair.com and save!
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.
Please visit this page again later or try out our merchant comparison search. Good luck!
Recently found cheap flight deals
Phoenix To Managua Multiple Airlines airfares from Phoenix in March
$2023 Depart: 03/08/2025
Return: 03/13/2025
provided by Cheapoair.com
Las Vegas To Spartanburg Alaska Airlines airfares from Las Vegas in August
$1020 Depart: 08/11/2024
Return: 08/19/2024
provided by Cheapoair.com
Phoenix To St Kitts Multiple Airlines airfares from Phoenix in October
$4581 Depart: 10/22/2023
Return: 10/28/2023
provided by Cheapoair.com
Ottawa To Honolulu Multiple Airlines airfares from Ottawa in October
$941 Depart: 10/30/2019
Return: 11/08/2019
provided by Cheapoair.com
Buffalo To Frankfurt Multiple Airlines airfares from Buffalo in April
$1012 Depart: 04/16/2025
Return: 04/25/2025
provided by Cheapoair.com
Las Vegas To Anaheim Multiple Airlines airfares from Las Vegas in April
$85 Depart: 04/15/2025
Return: 04/27/2025
provided by Cheapoair.com
Durham To Beijing Korean Air airfares from Durham in March
$2100 Depart: 03/12/2025
Return: 03/26/2025
provided by Cheapoair.com
Tampa To Vancouver Alaska Airlines airfares from Tampa in October
$804 Depart: 10/24/2023
Return: 10/29/2023
provided by Cheapoair.com
Pittsburgh To Los Angeles Mexicana Airlines airfares from Pittsburgh in April
$214 Depart: 04/02/2025
Return: 04/23/2025
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Chicago to San Jose, San Jose hotel rooms and Chicago to San Jose vacation packages from the most popular providers, airline consolidators and travel search engines.
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, [...]
© Copyright 2004 - 2025 Travelgrove, Inc.