Cheap flights from Chicago to San Diego from CA $59

View CA $59 flight on Tue, Aug. 19, 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 and start at CA $59 for one-way flights and CA $215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Oct. 23 - Sat, Nov. 1
ORD
Chicago
SAN
San Diego
CA $215 Roundtrip, found 5 days ago
CA $215
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Oct. 23 from Chicago to San Diego, returning Sat, Nov. 1, priced at CA $215 found 5 days ago
Alaska Airlines
Fri, Oct. 24 - Tue, Oct. 28
ORD
Chicago
SAN
San Diego
CA $223 Roundtrip, found 2 days ago
CA $223
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Fri, Oct. 24 from Chicago to San Diego, returning Tue, Oct. 28, priced at CA $223 found 2 days ago
Alaska Airlines
Fri, Oct. 24 - Tue, Oct. 28
ORD
Chicago
SAN
San Diego
CA $224 Roundtrip, found 2 days ago
CA $224
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Fri, Oct. 24 from Chicago to San Diego, returning Tue, Oct. 28, priced at CA $224 found 2 days ago
Hawaiian Airlines
Sat, Sep. 27 - Tue, Oct. 14
ORD
Chicago
SAN
San Diego
CA $237 Roundtrip, found 2 days ago
CA $237
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Sat, Sep. 27 from Chicago to San Diego, returning Tue, Oct. 14, priced at CA $237 found 2 days ago
Spirit Airlines
Thu, Oct. 23 - Sat, Nov. 1
ORD
Chicago
SAN
San Diego
CA $263 Roundtrip, found 5 days ago
CA $263
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Oct. 23 from Chicago to San Diego, returning Sat, Nov. 1, priced at CA $263 found 5 days ago
United
Sat, Sep. 13 - Sat, Sep. 27
ORD
Chicago
SAN
San Diego
CA $312 Roundtrip, found 2 days ago
CA $312
Roundtrip
found 2 days ago
Select United flight, departing Sat, Sep. 13 from Chicago to San Diego, returning Sat, Sep. 27, priced at CA $312 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 CA $122 - CA $287 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.