Cheap Flights from San Antonio to Chicago
Browse current best options from San Antonio. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
San Antonio
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 7 days ago
483 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)
Today’s best flight deals from San Antonio to Chicago
Explore current cheapest deals departing from San Antonio to Chicago
2026-11-10 – 2026-12-02
SAT - Chicago
50% AI deal score
$255
$223
Round trip
2026-11-11 – 2026-12-02
SAT - Chicago
49% AI deal score
$253
$223
Round trip
2026-11-10 – 2026-12-05
SAT - Chicago
49% AI deal score
$255
$228
Round trip
2026-11-10 – 2026-12-08
SAT - Chicago
49% AI deal score
$255
$228
Round trip
2026-11-11 – 2026-12-09
SAT - Chicago
49% AI deal score
$253
$228
Round trip
2026-11-16 – 2026-12-02
SAT - Chicago
47% AI deal score
$260
$248
Round trip
2026-11-16 – 2026-12-09
SAT - Chicago
45% AI deal score
$254
$254
Round trip
2026-11-16 – 2026-12-08
SAT - Chicago
45% AI deal score
$254
$254
Round trip
2026-11-16 – 2026-12-15
SAT - Chicago
45% AI deal score
$253
$254
Round trip
2026-11-21 – 2026-12-02
SAT - Chicago
45% AI deal score
$271
$273
Round trip
