Cheap Flights from San Diego to Chicago
Browse current best options from San Diego. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
San Diego
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 2 days ago
444 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Aug 9, 2026.)
Today’s best flight deals from San Diego to Chicago
Explore current cheapest deals departing from San Diego to Chicago
2026-11-05 – 2026-11-17
SAN - Chicago
71% AI deal score
$219
$179
Round trip
2026-10-13 – 2026-10-14
SAN - Chicago
78% AI deal score
$247
$180
Round trip
2026-09-17 – 2026-09-24
SAN - Chicago
80% AI deal score
$268
$184
Round trip
2026-11-05 – 2026-11-09
SAN - Chicago
81% AI deal score
$295
$186
Round trip
2026-10-20 – 2026-10-24
SAN - Chicago
80% AI deal score
$281
$188
Round trip
2026-10-15 – 2026-10-18
SAN - Chicago
81% AI deal score
$281
$188
Round trip
2026-11-10 – 2026-11-16
SAN - Chicago
77% AI deal score
$246
$188
Round trip
2026-11-03 – 2026-11-09
SAN - Chicago
80% AI deal score
$286
$190
Round trip
2026-10-02 – 2026-10-18
SAN - Chicago
77% AI deal score
$234
$191
Round trip
2026-11-10 – 2026-11-17
SAN - Chicago
72% AI deal score
$246
$194
Round trip
