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

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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 San Diego (SAN) to Chicago (CHI)

How to find the cheapest flight from San Diego (SAN) to Chicago (CHI)
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How to find the cheapest flight from San Diego (SAN) to Chicago (CHI)
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How to find the cheapest flight from San Diego (SAN) to Chicago (CHI)
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Cheap flights from San Diego to Chicago in March , April 2026

23 Mar - 15 Apr $ 201.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates
09 Mar - 08 Apr $ 321.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates
09 Mar - 01 Apr $ 321.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates

Last minute flights from San Diego to Chicago

23 Mar - 31 Mar $ 233.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates
11 Mar - 31 Mar $ 308.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates
11 Mar - 31 Mar $ 347.00
SAN
San Diego
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates

One-way flights to Chicago from San Diego

5:00 PM - 5:00 PM
United Airlines
0 Stops
3h 59m
SAN - CHI
$ 119
Kiwi
Pick dates
8:35 AM - 8:35 AM
Alaska Airlines
0 Stops
4h 23m
SAN - CHI
$ 207
Kiwi
Pick dates
5:00 PM - 5:00 PM
United Airlines
0 Stops
3h 59m
SAN - CHI
$ 209
Kiwi
Pick dates

How to find the cheapest flight from San Diego (SAN) to Chicago (CHI)

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