Cheap Flights from Chicago to San Jose

View €77 flight on Sat, 30 Aug 2025Opens in a new window

Popular airlines from Chicago to San Jose

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Cheap flights from Chicago to San Jose (CHI-SJC)

Prices were available within the past 7 days and start at €77 for one-way flights and €168 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 18 Oct - Sat, 25 Oct
ORD
Chicago
SFO
San Francisco
€168 Return, found 2 days ago
€168
Return
found 2 days ago
Select American Airlines flight, departing Sat, 18 Oct from Chicago to San Francisco, returning Sat, 25 Oct, priced at €168 found 2 days ago
American Airlines
Sat, 18 Oct - Mon, 20 Oct
ORD
Chicago
SFO
San Francisco
€177 Return, found 2 days ago
€177
Return
found 2 days ago
Select American Airlines flight, departing Sat, 18 Oct from Chicago to San Francisco, returning Mon, 20 Oct, priced at €177 found 2 days ago
American Airlines
Sat, 23 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
€184 Return, found 4 hours ago
€184
Return
found 4 hours ago
Select American Airlines flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at €184 found 4 hours ago
Delta
Sat, 23 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
€209 Return, found 4 hours ago
€209
Return
found 4 hours ago
Select Delta flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at €209 found 4 hours ago
United
Sat, 23 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
€222 Return, found 4 hours ago
€222
Return
found 4 hours ago
Select United flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at €222 found 4 hours ago
JetBlue Airways
Sat, 23 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
€748 Return, found 4 hours ago
€748
Return
found 4 hours ago
Select JetBlue Airways flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at €748 found 4 hours ago

Find the cheapest month to fly from Chicago (CHI) to San Jose (SJC)

September is typically the cheapest month to fly

From €87 - €315 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.