Lowest Prices
Uncover the best deals on Chicago to San Jose flights by comparing fares from hundreds of airlines and agencies.
Useful information for finding best airline tickets from Chicago O'Hare International to Juan Santamaria International on your next trip.
Cheapest Round Trip Flight
$598
Copa Airlines
• 1 stop
• 34h 9m
Dec 10 – Dec 17
The cheapest round trip flight from Chicago to San Jose (ORD-SJO-ORD) is currently $598
Fastest Flight
17h 16m
The fastest nonstop flight from Chicago to San Jose (ORD-SJO) takes 17h 16m
| Origin Airport | Chicago O'Hare International , Chicago, US |
| Destination Airport | Juan Santamaria International , San Jose, CR |
| Distance | 2214 miles |