Cheapest one-way flights from Chicago to Sydney in September from $1309

Best time to book flights for Chicago (MDW) to Sydney (SYD) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to Sydney (SYD) in September 2025 (see full year).

One-Way flights

13 Sep WestJet
26 Sep Korean Air

Also check the deals for return flights from Chicago to Sydney in September.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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