Cheap flights from Chicago to San Diego

View AU$108 flight on Tue, 9 Dec. 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
Fri, 22 Aug. - Tue, 26 Aug.
ORD
Chicago
SAN
San Diego
AU$257 Return, found 5 days ago
AU$257
Return
found 5 days ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Tue, 26 Aug., priced at AU$257 found 5 days ago
American Airlines
Fri, 22 Aug. - Mon, 25 Aug.
ORD
Chicago
SAN
San Diego
AU$294 Return, found 5 days ago
AU$294
Return
found 5 days ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Mon, 25 Aug., priced at AU$294 found 5 days ago
American Airlines
Fri, 22 Aug. - Tue, 26 Aug.
ORD
Chicago
SAN
San Diego
AU$339 Return, found 5 days ago
AU$339
Return
found 5 days ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Tue, 26 Aug., priced at AU$339 found 5 days ago
Delta
Fri, 22 Aug. - Mon, 25 Aug.
MDW
Chicago
SAN
San Diego
AU$391 Return, found 5 days ago
AU$391
Return
found 5 days ago
Select Delta flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Mon, 25 Aug., priced at AU$391 found 5 days ago
United
Fri, 22 Aug. - Tue, 26 Aug.
ORD
Chicago
SAN
San Diego
AU$393 Return, found 5 days ago
AU$393
Return
found 5 days ago
Select United flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Tue, 26 Aug., priced at AU$393 found 5 days ago
Alaska Airlines
Fri, 22 Aug. - Mon, 25 Aug.
ORD
Chicago
SAN
San Diego
AU$572 Return, found 5 days ago
AU$572
Return
found 5 days ago
Select Alaska Airlines flight, departing Fri, 22 Aug. from Chicago to San Diego, returning Mon, 25 Aug., priced at AU$572 found 5 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$135 - AU$298 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.