Flights to Oakland from Chicago

View ฿3,190 flight on Wed, 27 Aug 2025Opens in a new window

Popular airlines from Chicago to Oakland

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Cheap Flights from Chicago (CHI) to Oakland (SJC)

Prices were available within the past 7 days and start at ฿3,190 for one-way flights and ฿6,370 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 27 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
฿6,370 Return, found 5 days ago
฿6,370
Return
found 5 days ago
Select United flight, departing Wed, 27 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at ฿6,370 found 5 days ago
American Airlines
Wed, 27 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
฿6,380 Return, found 5 days ago
฿6,380
Return
found 5 days ago
Select American Airlines flight, departing Wed, 27 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at ฿6,380 found 5 days ago
Delta
Wed, 27 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
฿6,965 Return, found 5 days ago
฿6,965
Return
found 5 days ago
Select Delta flight, departing Wed, 27 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at ฿6,965 found 5 days ago
Delta
Sat, 23 Aug - Sat, 30 Aug
ORD
Chicago
SJC
San Jose
฿7,085 Return, found 6 days ago
฿7,085
Return
found 6 days ago
Select Delta flight, departing Sat, 23 Aug from Chicago to San Jose, returning Sat, 30 Aug, priced at ฿7,085 found 6 days ago
Delta
Wed, 27 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
฿7,150 Return, found 5 days ago
฿7,150
Return
found 5 days ago
Select Delta flight, departing Wed, 27 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at ฿7,150 found 5 days ago
United
Wed, 27 Aug - Sat, 30 Aug
ORD
Chicago
SFO
San Francisco
฿7,380 Return, found 5 days ago
฿7,380
Return
found 5 days ago
Select United flight, departing Wed, 27 Aug from Chicago to San Francisco, returning Sat, 30 Aug, priced at ฿7,380 found 5 days ago

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

October is typically the cheapest month to fly

From ฿3,394 - ฿10,622 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.