Cheap flights from Chicago to Livermore Valley Wine Country

View AU$152 flight on Sat, 4 Oct. 2025Opens in a new window

Popular airlines from Chicago to Livermore Valley Wine Country

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Cheap Flights from Chicago (CHI) to Livermore Valley Wine Country (SJC)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 30 Aug. - Sun, 31 Aug.
ORD
Chicago
SFO
San Francisco
AU$275 Return, found 6 days ago
AU$275
Return
found 6 days ago
Select American Airlines flight, departing Sat, 30 Aug. from Chicago to San Francisco, returning Sun, 31 Aug., priced at AU$275 found 6 days ago
American Airlines
Wed, 3 Sep. - Wed, 10 Sep.
ORD
Chicago
SFO
San Francisco
AU$305 Return, found 4 days ago
AU$305
Return
found 4 days ago
Select American Airlines flight, departing Wed, 3 Sep. from Chicago to San Francisco, returning Wed, 10 Sep., priced at AU$305 found 4 days ago
Alaska Airlines
Thu, 30 Oct. - Mon, 10 Nov.
ORD
Chicago
SFO
San Francisco
AU$362 Return, found 21 hours ago
AU$362
Return
found 21 hours ago
Select Alaska Airlines flight, departing Thu, 30 Oct. from Chicago to San Francisco, returning Mon, 10 Nov., priced at AU$362 found 21 hours ago
Delta
Thu, 30 Oct. - Mon, 10 Nov.
ORD
Chicago
SFO
San Francisco
AU$391 Return, found 21 hours ago
AU$391
Return
found 21 hours ago
Select Delta flight, departing Thu, 30 Oct. from Chicago to San Francisco, returning Mon, 10 Nov., priced at AU$391 found 21 hours ago
United
Sat, 30 Aug. - Sun, 31 Aug.
ORD
Chicago
SFO
San Francisco
AU$413 Return, found 6 days ago
AU$413
Return
found 6 days ago
Select United flight, departing Sat, 30 Aug. from Chicago to San Francisco, returning Sun, 31 Aug., priced at AU$413 found 6 days ago
Hawaiian Airlines
Sat, 2 Aug. - Wed, 6 Aug.
ORD
Chicago
SFO
San Francisco
AU$746 Return, found 6 days ago
AU$746
Return
found 6 days ago
Select Hawaiian Airlines flight, departing Sat, 2 Aug. from Chicago to San Francisco, returning Wed, 6 Aug., priced at AU$746 found 6 days ago

Find the cheapest month to fly from Chicago (CHI) to Oakland (OAK)

October is typically the cheapest month to fly

From AU$160 - AU$500 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.