Earn point on your loyalty program!arrow arc left

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

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 San Diego (SAN) to Chicago (CHI)

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.
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.

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

20 Oct - 10 Nov $ 342.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
22 Oct - 25 Nov $ 388.00
SAN
San Diego
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
SAN
San Diego
Pick dates
25 Oct - 10 Nov $ 536.00
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

20 Oct - 31 Oct $ 389.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
23 Oct - 31 Oct $ 396.00
SAN
San Diego
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
SAN
San Diego
Pick dates
24 Oct - 31 Oct $ 730.00
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

8:34 PM - 11:29 PM
Frontier Airlines
1 Stops
6h 42m
SAN - CHI
$ 208
Kiwi
Pick dates
10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 3m
SAN - CHI
$ 302
Kiwi
Pick dates
10:30 PM - 10:30 PM
United Airlines
0 Stops
4h 3m
SAN - CHI
$ 302
Kiwi
Pick dates

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

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 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.