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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 April , May 2026

24 Apr - 23 May $ 175.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
12 Apr - 06 May $ 442.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
03 Apr - 18 May $ 692.00
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
Pick dates

Last minute flights from San Diego to Chicago

23 Apr - 30 Apr $ 175.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
12 Apr - 30 Apr $ 617.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SAN
San Diego
Pick dates
03 Apr - 30 Apr $ 712.00
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
Pick dates

One-way flights to Chicago from San Diego

10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 5m
SAN - CHI
$ 109
Kiwi
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2:10 PM - 2:10 PM
United Airlines
0 Stops
4h 12m
SAN - CHI
$ 334
Kiwi
Pick dates
10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 5m
SAN - CHI
$ 347
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.