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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 September , October 2026

29 Sep - 03 Oct $ 325.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
30 Sep - 28 Oct $ 329.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
28 Sep - 12 Oct $ 670.00
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

29 Sep - 30 Sep $ 325.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
29 Sep - 30 Sep $ 403.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
29 Sep - 30 Sep $ 528.00
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

5:54 PM - 11:50 PM
Frontier Airlines
1 Stops
9h 44m
SAN - CHI
$ 162
Kiwi
Pick dates
10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 3m
SAN - CHI
$ 199
Kiwi
Pick dates
10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 3m
SAN - CHI
$ 200
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.