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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 May , June 2026

28 May - 06 Jun $ 295.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
24 May - 06 Jun $ 295.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
24 May - 10 Jun $ 350.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates

Last minute flights from San Diego to Chicago

29 May - 31 May $ 390.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
24 May - 31 May $ 390.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
17 May - 31 May $ 697.00
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
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One-way flights to Chicago from San Diego

5:44 PM - 5:44 PM
Alaska Airlines
0 Stops
4h 11m
SAN - CHI
$ 172
Kiwi
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7:00 AM - 7:00 AM
Alaska Airlines
0 Stops
4h 14m
SAN - CHI
$ 172
Kiwi
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10:40 PM - 10:40 PM
United Airlines
0 Stops
4h 5m
SAN - CHI
$ 379
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.