Cheap flights from Chicago to San Diego

View AU$108 flight on Sat, 11 Oct. 2025Opens in a new window

Popular airlines from Chicago to San Diego

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Cheap Flights from Chicago (CHI) to San Diego (SAN)

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.

Hawaiian Airlines
Fri, 24 Oct. - Mon, 27 Oct.
ORD
Chicago
SAN
San Diego
AU$205 Return, found 5 days ago
AU$205
Return
found 5 days ago
Select Hawaiian Airlines flight, departing Fri, 24 Oct. from Chicago to San Diego, returning Mon, 27 Oct., priced at AU$205 found 5 days ago
Hawaiian Airlines
Tue, 21 Oct. - Tue, 11 Nov.
ORD
Chicago
SAN
San Diego
AU$215 Return, found 4 days ago
AU$215
Return
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, 21 Oct. from Chicago to San Diego, returning Tue, 11 Nov., priced at AU$215 found 4 days ago
Alaska Airlines
Fri, 3 Oct. - Tue, 14 Oct.
ORD
Chicago
SAN
San Diego
AU$275 Return, found 4 days ago
AU$275
Return
found 4 days ago
Select Alaska Airlines flight, departing Fri, 3 Oct. from Chicago to San Diego, returning Tue, 14 Oct., priced at AU$275 found 4 days ago
American Airlines
Tue, 9 Sep. - Wed, 10 Sep.
ORD
Chicago
SAN
San Diego
AU$282 Return, found 6 days ago
AU$282
Return
found 6 days ago
Select American Airlines flight, departing Tue, 9 Sep. from Chicago to San Diego, returning Wed, 10 Sep., priced at AU$282 found 6 days ago
United
Tue, 9 Sep. - Wed, 10 Sep.
ORD
Chicago
SAN
San Diego
AU$321 Return, found 6 days ago
AU$321
Return
found 6 days ago
Select United flight, departing Tue, 9 Sep. from Chicago to San Diego, returning Wed, 10 Sep., priced at AU$321 found 6 days ago
Delta
Thu, 4 Sep. - Wed, 10 Sep.
ORD
Chicago
SAN
San Diego
AU$394 Return, found 3 days ago
AU$394
Return
found 3 days ago
Select Delta flight, departing Thu, 4 Sep. from Chicago to San Diego, returning Wed, 10 Sep., priced at AU$394 found 3 days ago

Find the cheapest month to fly from Chicago (CHI) to San Diego (SAN)

September is typically the cheapest month to fly

From AU$133 - AU$287 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.