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

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)

How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)
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How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)
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How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)
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Cheap flights from Chicago to San Diego in December 2025 , January 2026

25 Dec - 08 Jan $ 337.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
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25 Dec - 10 Jan $ 354.00
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
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16 Dec - 18 Jan $ 1,025.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to San Diego

25 Dec - 31 Dec $ 407.00
CHI
Chicago
United Airlines
1 STOPS
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates
25 Dec - 31 Dec $ 437.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates
23 Dec - 31 Dec $ 492.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to San Diego from Chicago

7:10 AM - 7:10 AM
United Airlines
0 Stops
4h 34m
CHI - SAN
$ 204
Kiwi
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10:56 AM - 4:02 PM
United Airlines
1 Stops
8h 38m
CHI - SAN
$ 215
Kiwi
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8:55 AM - 8:55 AM
Alaska Airlines
0 Stops
4h 27m
CHI - SAN
$ 382
Kiwi
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How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)

Related info for your journey
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How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.