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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 January , February 2026

31 Jan - 14 Feb $ 228.00
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
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21 Jan - 03 Feb $ 285.00
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
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21 Jan - 10 Feb $ 285.00
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
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Last minute flights from Chicago to San Diego

27 Jan - 31 Jan $ 297.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates
20 Jan - 31 Jan $ 357.00
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
22 Jan - 31 Jan $ 450.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
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One-way flights to San Diego from Chicago

7:10 AM - 7:10 AM
United Airlines
0 Stops
4h 30m
CHI - SAN
$ 149
Kiwi
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9:00 AM - 9:00 AM
Alaska Airlines
0 Stops
4h 43m
CHI - SAN
$ 207
Kiwi
Pick dates
7:10 AM - 7:10 AM
United Airlines
0 Stops
4h 30m
CHI - SAN
$ 209
Kiwi
Pick dates

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.