Cheap flights from Chicago to San Diego

View AU$108 flight on Tue, 11 Nov. 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.

American Airlines
Sat, 4 Oct. - Sat, 11 Oct.
ORD
Chicago
SAN
San Diego
AU$214 Return, found 2 days ago
AU$214
Return
found 2 days ago
Select American Airlines flight, departing Sat, 4 Oct. from Chicago to San Diego, returning Sat, 11 Oct., priced at AU$214 found 2 days ago
Alaska Airlines
Sat, 4 Oct. - Sat, 11 Oct.
ORD
Chicago
SAN
San Diego
AU$254 Return, found 2 days ago
AU$254
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 4 Oct. from Chicago to San Diego, returning Sat, 11 Oct., priced at AU$254 found 2 days ago
American Airlines
Thu, 18 Sep. - Sat, 20 Sep.
ORD
Chicago
SAN
San Diego
AU$259 Return, found 2 days ago
AU$259
Return
found 2 days ago
Select American Airlines flight, departing Thu, 18 Sep. from Chicago to San Diego, returning Sat, 20 Sep., priced at AU$259 found 2 days ago
American Airlines
Thu, 11 Sep. - Sat, 13 Sep.
ORD
Chicago
SAN
San Diego
AU$282 Return, found 3 days ago
AU$282
Return
found 3 days ago
Select American Airlines flight, departing Thu, 11 Sep. from Chicago to San Diego, returning Sat, 13 Sep., priced at AU$282 found 3 days ago
United
Sat, 4 Oct. - Sat, 11 Oct.
ORD
Chicago
SAN
San Diego
AU$284 Return, found 2 days ago
AU$284
Return
found 2 days ago
Select United flight, departing Sat, 4 Oct. from Chicago to San Diego, returning Sat, 11 Oct., priced at AU$284 found 2 days ago
Delta
Sat, 4 Oct. - Sat, 11 Oct.
ORD
Chicago
SAN
San Diego
AU$359 Return, found 2 days ago
AU$359
Return
found 2 days ago
Select Delta flight, departing Sat, 4 Oct. from Chicago to San Diego, returning Sat, 11 Oct., priced at AU$359 found 2 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$141 - AU$301 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.