Cheap flights from Chicago to Livermore Valley Wine Country

View AU$150 flight on Tue, 19 Aug. 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
Sun, 7 Sep. - Wed, 8 Oct.
ORD
Chicago
SFO
San Francisco
AU$315 Return, found 7 hours ago
AU$315
Return
found 7 hours ago
Select American Airlines flight, departing Sun, 7 Sep. from Chicago to San Francisco, returning Wed, 8 Oct., priced at AU$315 found 7 hours ago
American Airlines
Thu, 30 Oct. - Mon, 10 Nov.
ORD
Chicago
SFO
San Francisco
AU$333 Return, found 4 days ago
AU$333
Return
found 4 days ago
Select American Airlines flight, departing Thu, 30 Oct. from Chicago to San Francisco, returning Mon, 10 Nov., priced at AU$333 found 4 days ago
Alaska Airlines
Thu, 30 Oct. - Mon, 10 Nov.
ORD
Chicago
SFO
San Francisco
AU$362 Return, found 4 days ago
AU$362
Return
found 4 days ago
Select Alaska Airlines flight, departing Thu, 30 Oct. from Chicago to San Francisco, returning Mon, 10 Nov., priced at AU$362 found 4 days ago
Delta
Thu, 30 Oct. - Mon, 10 Nov.
ORD
Chicago
SFO
San Francisco
AU$391 Return, found 4 days ago
AU$391
Return
found 4 days ago
Select Delta flight, departing Thu, 30 Oct. from Chicago to San Francisco, returning Mon, 10 Nov., priced at AU$391 found 4 days ago
United
Sun, 7 Sep. - Wed, 8 Oct.
ORD
Chicago
SFO
San Francisco
AU$412 Return, found 7 hours ago
AU$412
Return
found 7 hours ago
Select United flight, departing Sun, 7 Sep. from Chicago to San Francisco, returning Wed, 8 Oct., priced at AU$412 found 7 hours ago
Hawaiian Airlines
Mon, 4 Aug. - Tue, 12 Aug.
ORD
Chicago
SFO
San Francisco
AU$799 Return, found 1 day ago
AU$799
Return
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, 4 Aug. from Chicago to San Francisco, returning Tue, 12 Aug., priced at AU$799 found 1 day 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.