Cheap Flights from Sydney to Chicago
Browse current best options from Sydney. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Sydney
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
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 Sydney to Chicago
Explore current cheapest deals departing from Sydney to Chicago
2026-10-23 – 2026-10-30
SYD - Chicago
91% AI deal score
A$1,962
A$1,234
Round trip
2026-10-19 – 2026-10-28
SYD - Chicago
91% AI deal score
A$1,910
A$1,237
Round trip
2026-10-05 – 2026-10-19
SYD - Chicago
90% AI deal score
A$1,859
A$1,383
Round trip
2026-10-01 – 2026-10-26
SYD - Chicago
89% AI deal score
A$1,849
A$1,410
Round trip
2026-10-08 – 2026-10-21
SYD - Chicago
89% AI deal score
A$1,860
A$1,443
Round trip
2026-10-14 – 2026-10-20
SYD - Chicago
90% AI deal score
A$1,966
A$1,456
Round trip
2026-10-12 – 2026-10-24
SYD - Chicago
89% AI deal score
A$1,871
A$1,456
Round trip
2026-11-05 – 2026-11-19
SYD - Chicago
89% AI deal score
A$1,845
A$1,456
Round trip
2026-10-26 – 2026-10-29
SYD - Chicago
90% AI deal score
A$2,044
A$1,462
Round trip
2026-10-14 – 2026-10-28
SYD - Chicago
88% AI deal score
A$1,866
A$1,462
Round trip
