January is by far the best month, wherein you can get cheapest flights for Chicago to San Jose. Meanwhile, is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
Disclaimer - All the above-mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

Chicago
10:00
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
23:15
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
12:50
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
23:15
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
05:30
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
22:15
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
17:30
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
22:30
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
08:10
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
19:44
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
05:30
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
13:00
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
07:35
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
21:52
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
14:13
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
07:06
San Jose
Juan Santamaria International Airport
Mon, 19 Jan 2026

Chicago
14:13
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
21:52
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
00:59
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
12:04
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026

Chicago
14:35
Chicago
Chicago O Hare International Airport
Sun , 18 Jan 2026

San Jose
21:50
San Jose
Juan Santamaria International Airport
Sun, 18 Jan 2026










Flying from Chicago to San Jose has never been easier. Whether you’re planning a short business trip, a weekend getaway, or reconnecting with family and friends, Easemytrip brings you the best deals, seamless booking, and flexible options for this popular flight route. Our platform is built to help travellers like you compare flight prices, explore direct and connecting options, and find the perfect departure time — all within a few clicks.
The air route between Chicago to San Jose is one of the most frequently travelled, offering reliable services from top airlines and excellent connectivity between Chicago O Hare International Airport (ORD) and Juan Santamaria International Airport (SJO). You can expect a flight distance of approximately 3574 km, and most direct services cover it in around 11:03.
Let’s take a closer look at everything you need to know before booking your flight from Chicago to San Jose.
| Flight Details | Information |
|---|---|
| Route Distance | 3574 km |
| Average Flight Time | 11:03 hrs |
| Departure Airport | Chicago O Hare International Airport (ORD) |
| Arrival Airport | Juan Santamaria International Airport (SJO) |
| Cabin Classes Available | Economy Class, Premium Economy, Business Class, First Class |
| Direct Flights | YES |
| Common Airlines | Air Canada, Delta Airlines, American Airlines, Copa Airlines |
The route is serviced regularly by both full-service and budget airlines, catering to all types of travellers — from those looking for no-frills budget options to those preferring business and first-class comfort. If you're flying for business, early morning weekday flights are a great choice, while leisure travellers often opt for weekend and evening departures.