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 today
485 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Nov 2, 2026.)
Today’s best flight deals from Sydney to Chicago
Explore current cheapest deals departing from Sydney to Chicago
2026-11-07 – 2026-11-14
SYD - Chicago
81% AI deal score
A$2,100
A$1,888
Round trip
2026-11-01 – 2026-11-08
SYD - Chicago
82% AI deal score
A$2,173
A$1,889
Round trip
2026-11-15 – 2026-11-30
SYD - Chicago
77% AI deal score
A$1,865
A$1,893
Round trip
2027-01-26 – 2027-02-25
SYD - Chicago
76% AI deal score
A$1,997
A$1,919
Round trip
2027-01-26 – 2027-02-20
SYD - Chicago
76% AI deal score
A$1,997
A$1,919
Round trip
2027-01-26 – 2027-02-24
SYD - Chicago
75% AI deal score
A$1,997
A$1,942
Round trip
2027-01-26 – 2027-02-17
SYD - Chicago
76% AI deal score
A$2,008
A$1,943
Round trip
2027-01-26 – 2027-02-16
SYD - Chicago
76% AI deal score
A$2,008
A$1,943
Round trip
2027-01-26 – 2027-02-14
SYD - Chicago
75% AI deal score
A$2,010
A$1,947
Round trip
2027-01-26 – 2027-02-13
SYD - Chicago
75% AI deal score
A$2,011
A$1,979
Round trip
