Cheap flights from Chicago to Sydney from $539
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sydney departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Fri 3/5
6:29 am-9:50 am
2 stops34h 21m
Sydney Kingsford Smith
Tue 3/16
11:30 am-5:55 pm
1 stop46h 25m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 2/28
5:00 am-9:50 am
2 stops35h 50m
Sydney Kingsford Smith
Thu 3/11
11:30 am-4:55 pm
1 stop46h 25m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Tue 11/3
9:21 am-8:35 am
2 stops30h 14m
Sydney Kingsford Smith
Tue 11/10
9:55 am-8:35 pm
2 stops27h 40m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 2/7
12:45 pm-8:35 am
2 stops26h 50m
Sydney Kingsford Smith
Sun 2/21
11:50 am-6:25 am
2 stops35h 35m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Tue 3/23
3:40 pm-8:35 am
1 stop24h 55m
Sydney Kingsford Smith
Tue 4/6
9:20 am-2:35 pm
1 stop20h 15m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Tue 2/9
8:58 am-9:35 am
1 stop31h 37m
Sydney Kingsford Smith
Mon 2/15
11:20 am-2:32 pm
1 stop20h 12m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 4/4
5:45 pm-9:25 am
1 stop24h 40m
Sydney Kingsford Smith
Mon 4/12
8:55 pm-8:40 am
1 stop26h 45m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Mon 3/15
5:25 pm-10:30 am
1 stop25h 05m
Sydney Kingsford Smith
Wed 4/14
8:55 pm-8:40 am
1 stop26h 45m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Mon 10/19
10:30 am-7:30 am
1 stop29h 00m
Sydney Kingsford Smith
Wed 11/4
2:05 pm-8:00 pm
1 stop22h 55m
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Tue 12/29
9:18 pm-9:00 am
1 stop42h 42m
Sydney Kingsford Smith
Tue 2/2
11:20 am-6:28 pm
1 stop24h 08m
See travel insights to Sydney from
How to get the cheapest flight ticket from Chicago to Sydney
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Sydney?
Prices are currently low for flights on this route.
Typical prices usually range from $1,320 to $1,792.The lowest price recently found on this route was $1,292.
What is the cheapest month to fly to Sydney?
In general, February is the cheapest month to fly from Chicago to Sydney. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $1,230. If you are unable to visit Sydney during the month of February, then departing from Chicago during the month June is also very affordable. Most momondo users find prices during this month for around $1,278.
How far in advance should I book a flight from Chicago to Sydney?
You are more likely to see cheaper flights to Sydney from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sydney for around $1,422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sydney from Chicago for as low as $1,055 on momondo.
Can stopping save me money on Chicago to Sydney flights?
You could potentially save up to 1% on your flight if you consider stops on a Chicago to Sydney flight.
How have Chicago to Sydney flight prices changed over time?
As of October 2026, prices for Chicago to Sydney flights are approximately 11% cheaper when compared to flights at the same time last year.
Which airport is the most popular layover for flights between Chicago and Sydney?
Los Angeles (LAX) was the most common stop: 63% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Chicago to Sydney?
Flights via Vancouver (YVR) offer the lowest average round-trip price of $1,160.
Which layover airport has the shortest travel time from Chicago to Sydney?
Flights connecting via Dallas (DFW) have the shortest average one-way travel time: 20h 55m.
Which layover airport has the shortest connection time from Chicago to Sydney?
Dallas (DFW) has the shortest average layover time for this route: 1h 39m.
When to book flights from Chicago to Sydney
Cheap Chicago to Sydney (CHI to SYD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Sydney
Frequently asked questions about flying from Chicago to Sydney
How far is Chicago to Sydney Kingsford Smith by plane?
There are 9237.5 mi between Chicago and Sydney Kingsford Smith. By plane, this route typically takes 24h 35m.
When did momondo last update prices for flights from Chicago to Sydney Kingsford Smith Airport?
Prices for flights from Chicago to Sydney Kingsford Smith Airport were last updated today.
How many operators does momondo search for flights from Chicago to Sydney Kingsford Smith Airport?
As of October 2026, there are 8 operators available to choose from for flights from Chicago to Sydney Kingsford Smith Airport.
How old do you have to be to fly from Chicago to Sydney Kingsford Smith Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Sydney Kingsford Smith Airport.
What documentation or ID do you need to fly to Sydney Kingsford Smith Airport?
The required travel and health documents for your Sydney Kingsford Smith Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Sydney Kingsford Smith Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular airline from Chicago to Sydney?
Based on momondo bookings for flights between Chicago and Sydney, the leading airline is Qantas Airways, making up 42% of the total bookings. Other popular airlines include United Airlines with 17%, Air Canada with 14%, and American Airlines with 10%.
Best airlines flying from Chicago to Sydney
Compare and see reviews for airlines that fly from Chicago to Sydney with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $237 | Free Cancellation | Rating 7.8 8,652 reviews | |||
| PriceFrom $716 | Free Cancellation | Rating 8.0 259 reviews | |||
| PriceFrom $837 | Free Cancellation | Rating 7.5 1,106 reviews | |||
| PriceFrom $837 | Free Cancellation | Rating 7.0 12,149 reviews | |||
| PriceFrom $870 | Free Cancellation | Rating 7.4 10,330 reviews | |||
| PriceFrom $1,120 | Free Cancellation | Rating 7.1 11,748 reviews | |||
| PriceFrom $1,193 | Free Cancellation | Rating 8.3 1,321 reviews | |||
| PriceFrom $1,294 | Free Cancellation | Rating 8.0 671 reviews |
Traveling to a place near Sydney?
Book flights to Sydney if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Sydney?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Sydney for you.
Can I find flights from Chicago to Sydney with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Sydney from Chicago with this policy.
How can momondo help me find flights from Chicago to Sydney?
Once you have performed a search for Chicago to Sydney flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Chicago to Sydney right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Sydney flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.