Earn point on your loyalty program!arrow arc left

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

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

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

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

Cheap flights from Chicago to San Diego in October , November 2026

28 Oct - 10 Nov $ 325.00
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
22 Oct - 24 Nov $ 389.00
CHI
Chicago
Alaska Airlines
1 STOPS
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
19 Oct - 16 Nov $ 680.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to San Diego

28 Oct - 31 Oct $ 414.00
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
26 Oct - 31 Oct $ 518.00
CHI
Chicago
Alaska Airlines
1 STOPS
SAN
San Diego
SAN
San Diego
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
24 Oct - 31 Oct $ 730.00
CHI
Chicago
United Airlines
DIRECT
SAN
San Diego
SAN
San Diego
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to San Diego from Chicago

6:30 AM - 2:28 PM
Frontier Airlines
1 Stops
11h 28m
CHI - SAN
$ 188
Kiwi
Pick dates
3:30 PM - 6:27 PM
Frontier Airlines
1 Stops
6h 19m
CHI - SAN
$ 208
Kiwi
Pick dates
1:30 PM - 1:30 PM
United Airlines
0 Stops
4h 19m
CHI - SAN
$ 302
Kiwi
Pick dates

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

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