American Airlines Cheap Flights from Chicago to San Jose

View €156 flight on Wed, 29 Oct 2025Opens in a new window
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Prices were available within the past 7 days and start at €156 for one-way flights and €302 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€302 Return, found 2 hours ago
€302
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €302 found 2 hours ago
American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€308 Return, found 2 hours ago
€308
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €308 found 2 hours ago
American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€323 Return, found 2 hours ago
€323
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €323 found 2 hours ago
American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€352 Return, found 2 hours ago
€352
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €352 found 2 hours ago
American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€355 Return, found 2 hours ago
€355
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €355 found 2 hours ago
American Airlines
Sat, 25 Oct - Wed, 29 Oct
ORD
Chicago
SJC
San Jose
€361 Return, found 2 hours ago
€361
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Chicago to San Jose, returning Wed, 29 Oct, priced at €361 found 2 hours ago
Chicago to San Jose route information
Origin airport
O'Hare Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Distance
2919 km
Average flight time
5 hours 3 mins

Frequently asked questions

How much is an American Airlines flight from O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
You'll discover cheap return American Airlines flights from €302 from ORD to SJC by sorting your results from "Price (lowest to highest)" on Expedia. Or search for bargains from €156 for a one-way journey.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from ORD to SJC with American Airlines?
American Airlines flights to San Jose are generally more affordable in the low-season months of April and November. Whether you're after a one-way or a return ticket, you could land a better deal then.
Does American Airlines fly nonstop from O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
Click on our "Nonstop" filter when searching for direct American Airlines flights from ORD to SJC. You'll also be able to compare other airlines servicing the same direct trip.
What airports does American Airlines fly into in San Jose?
Board an American Airlines flight from O'Hare Intl. Airport (ORD) to San Jose, and you'll likely come in to Norman Y. Mineta San Jose Intl. Airport (SJC). This is the airline's primary hub in this city.
Can I change or cancel my American Airlines flight from O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
Depending on the type of fare you purchased, a fee is typically charged if you modify or cancel your booking more than 24 hours after it's been confirmed. To secure flexible plane tickets, select our "No cancel fee" or "Changes included" filter while looking for flights. For additional information on cancelling or modifying your reservation, head to "Trips," select your flight and click on "Manage Booking."
*Available to Expedia members.