Cheap Flights from Chicago to San Jose

View €86 flight on Sat, 23 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 €86 for one-way flights and €164 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 23 Aug - Sun, 31 Aug
ORD
Chicago
SFO
San Francisco
€164 Return, found 3 hours ago
€164
Return
found 3 hours ago
Select American Airlines flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sun, 31 Aug, priced at €164 found 3 hours ago
American Airlines
Sat, 18 Oct - Sat, 25 Oct
ORD
Chicago
SFO
San Francisco
€168 Return, found 4 days ago
€168
Return
found 4 days ago
Select American Airlines flight, departing Sat, 18 Oct from Chicago to San Francisco, returning Sat, 25 Oct, priced at €168 found 4 days ago
American Airlines
Sat, 18 Oct - Mon, 20 Oct
ORD
Chicago
SFO
San Francisco
€177 Return, found 4 days ago
€177
Return
found 4 days ago
Select American Airlines flight, departing Sat, 18 Oct from Chicago to San Francisco, returning Mon, 20 Oct, priced at €177 found 4 days ago
Delta
Sat, 23 Aug - Sun, 31 Aug
ORD
Chicago
SFO
San Francisco
€189 Return, found 3 hours ago
€189
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sun, 31 Aug, priced at €189 found 3 hours ago
United
Sat, 23 Aug - Sun, 31 Aug
ORD
Chicago
SFO
San Francisco
€228 Return, found 3 hours ago
€228
Return
found 3 hours ago
Select United flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sun, 31 Aug, priced at €228 found 3 hours ago
JetBlue Airways
Sat, 23 Aug - Sun, 31 Aug
ORD
Chicago
SFO
San Francisco
€765 Return, found 3 hours ago
€765
Return
found 3 hours ago
Select JetBlue Airways flight, departing Sat, 23 Aug from Chicago to San Francisco, returning Sun, 31 Aug, priced at €765 found 3 hours ago

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

September is typically the cheapest month to fly

From €88 - €300 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.