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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 July , August 2026

28 Jul - 02 Aug $ 326.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
28 Jul - 15 Aug $ 336.00
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
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24 Jul - 16 Aug $ 600.00
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

28 Jul - 01 Aug $ 354.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
28 Jul - 31 Jul $ 378.00
SAN
San Diego
Hawaiian Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
SAN
San Diego
Pick dates
25 Jul - 31 Jul $ 540.00
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

10:00 AM - 5:05 PM
Frontier Airlines
1 Stops
8h 52m
SAN - CHI
$ 148
Kiwi
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6:35 AM - 1:25 PM
Frontier Airlines
1 Stops
7h 33m
SAN - CHI
$ 149
Kiwi
Pick dates
10:25 PM - 10:25 PM
United Airlines
0 Stops
4h 11m
SAN - CHI
$ 211
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.