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
$348
Copa Airlines
• 1 stop
• 14h 4m
Aug 02 – Aug 08
The cheapest round trip flight from Chicago to San Jose (ORD-SJO-ORD) is currently $348
Fastest Flight
13h 55m
The fastest nonstop flight from Chicago to San Jose (ORD-SJO) takes 13h 55m
| Origin Airport | Chicago O'Hare International , Chicago, US |
| Destination Airport | Juan Santamaria International , San Jose, CR |
| Distance | 2214 miles |