- Cheapest from
- Sydney
- Cheapest month
- November
- Direct flights
- Not recently
$815 · Fiji Airways
November 2026
Usually 1+ stop
Flights to Chicago from each city
Lowest one-way fare per person over the coming months, in AUD. Choose a city to see every month and date.
Plan the rest of your trip to Chicago
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Getting around
About flights to Chicago
We compare the lowest fares to Chicago (CHI) from 2 cities across Australia and New Zealand, using prices travellers found in the last 48 hours. Right now the cheapest way there is from Sydney, from $815 one way, and November 2026 is looking like the cheapest month to go.
Fares move quickly, so if you spot a good price it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
What's the cheapest city to fly to Chicago from?
Sydney currently has the cheapest fares, from $815 one way in November 2026. Next cheapest: Melbourne ($918).
When is the cheapest time to fly to Chicago?
November 2026 has the lowest fares from the most cities right now. Open a city's route page to see every month.
Can I fly direct to Chicago?
We haven't seen direct fares from Australia and New Zealand recently, so most trips include at least one stop.