Cheap Flights from Chicago to Sydney
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Sydney
Prices updated 1 day ago
461 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)
Today’s best flight deals from Chicago to Sydney
Explore current cheapest deals departing from Chicago to Sydney
2026-11-11 – 2026-11-18
CHI - Sydney
76% AI deal score
$1,171
$1,100
Round trip
2026-11-16 – 2026-11-18
CHI - Sydney
77% AI deal score
$1,220
$1,100
Round trip
2026-11-02 – 2026-11-17
CHI - Sydney
74% AI deal score
$1,129
$1,109
Round trip
2026-11-07 – 2026-11-13
CHI - Sydney
75% AI deal score
$1,166
$1,143
Round trip
2026-11-04 – 2026-11-18
CHI - Sydney
73% AI deal score
$1,131
$1,156
Round trip
2026-11-01 – 2026-11-22
CHI - Sydney
74% AI deal score
$1,188
$1,213
Round trip
2026-11-12 – 2026-11-15
CHI - Sydney
77% AI deal score
$1,279
$1,218
Round trip
2027-02-17 – 2027-02-24
CHI - Sydney
74% AI deal score
$1,185
$1,226
Round trip
2027-03-02 – 2027-03-07
CHI - Sydney
74% AI deal score
$1,225
$1,228
Round trip
2027-03-03 – 2027-03-15
CHI - Sydney
74% AI deal score
$1,227
$1,230
Round trip
