Cheap flights from Sydney to Chicago

One-way fares from $815 · SYD → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Sydney
Cheapest fare
$815

Fiji Airways · Sun, 15 Nov

Cheapest month
November

from $815

Direct flights
Not recently

Usually 1+ stop

Quickest trip
20h 10m

14,880 km

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Cheapest month to fly from Sydney to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $815

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Fiji Airways
Depart14:00 Sun, 15 NovSYD → MDW 20h 10m · 3 stops
$815one way, per person
View deal
See every date in November 2026 →

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Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in ChicagoTours, attractions and day trips on Klook Explore →

Getting around

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About flights from Sydney to Chicago

Sydney (SYD) and Chicago (CHI) are about 14,880 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 20h 10m. Over the next few months, one-way fares start from $815, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Sydney to Chicago?

The cheapest one-way fare we've seen recently is $815 with Fiji Airways, departing Sunday 15 November 2026.

What is the cheapest month to fly from Sydney to Chicago?

November 2026 currently has the lowest fares, from $815 one way.

Are there direct flights from Sydney to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Sydney to Chicago?

The quickest journey we've seen takes about 20h 10m. Sydney and Chicago are around 14,880 km apart.

Which airlines fly from Sydney to Chicago?

Recent fares on this route were with Fiji Airways.

More cheap flights from Sydney

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