Which airport is the most popular for stopovers for flights between Sydney and Chicago?

Los Angeles (LAX) was the most common stop: 64% of momondo users choosing one-stop flights on this route connected there.

Which stopover airport has the shortest travel time from Sydney to Chicago?

Flights connecting via Vancouver (YVR) have the shortest average one-way travel time: 20h 21m.

Which stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Los Angeles (LAX) offer the lowest average return price of $1,205.

Which airlines fly to Chicago?

Qantas Airways, Air Canada and United Airlines are the top three most popular airlines that fly to Chicago from Sydney according to our data. Qantas Airways is the first choice among our users, with 63% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which stopover airport has the shortest connection time from Sydney to Chicago?

Dallas (DFW) has the shortest average stopover time for this route: 2h 10m.

What is the cheapest airline that flies from Sydney Kingsford Smith to Chicago?

Etihad Airways, Air New Zealand, and Air Canada are the most popular carriers operating from Sydney Kingsford Smith to Chicago

When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago?

Prices for flights from Sydney Kingsford Smith Airport to Chicago were last updated today.

How many operators does momondo search for flights from Sydney Kingsford Smith Airport to Chicago?

The number of operators available for flights from Sydney Kingsford Smith Airport to Chicago is 6 as of October 2025.

How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago?

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 Sydney Kingsford Smith Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$883 Cheap Flights from Sydney to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Sydney and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $1,524 to $2,064. The lowest price recently found on this route was $1,483.

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13:55 - 19:30SYD-ORD

22h 35m2 stops

14:30 - 08:45ORD-SYD

25h 15m2 stops

$1,483Air New Zealand

Find Deal

Sat, 8 Nov - Sun, 23 Nov

13:55 - 19:30SYD-ORD

22h 35m2 stops

13:00 - 08:45ORD-SYD

26h 45m2 stops

$1,593Air New Zealand

Find Deal

Mon, 3 Nov - Sat, 8 Nov

11:20 - 14:41SYD-ORD

20h 21m1 stop

15:40 - 09:35ORD-SYD

24h 55m1 stop

$1,665Air Canada

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Wed, 12 Nov - Thu, 27 Nov

11:20 - 14:41SYD-ORD

20h 21m1 stop

18:03 - 09:00ORD-SYD

21h 57m1 stop

$1,703Multiple Airlines

Find Deal

Thu, 13 Nov - Fri, 14 Nov

11:20 - 16:08SYD-ORD

21h 48m1 stop

08:50 - 09:00ORD-SYD

31h 10m1 stop

$1,736Qantas Airways

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Tue, 2 Dec - Tue, 9 Dec

11:20 - 21:24SYD-ORD

27h 04m1 stop

11:40 - 09:00ORD-SYD

28h 20m1 stop

$1,739Qantas Airways

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Mon, 17 Nov - Mon, 1 Dec

17:45 - 23:00SYD-ORD

22h 15m1 stop

20:18 - 07:25ORD-SYD

42h 07m1 stop

$1,763Multiple Airlines

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Sat, 8 Nov - Sun, 23 Nov

11:20 - 19:40SYD-ORD

25h 20m2 stops

21:42 - 09:00ORD-SYD

42h 18m1 stop

$1,816American Airlines

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Tue, 18 Nov - Sat, 29 Nov

11:20 - 20:00SYD-ORD

25h 40m2 stops

10:38 - 09:35ORD-SYD

29h 57m2 stops

$1,824Air Canada

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Wed, 12 Nov - Thu, 27 Nov

11:20 - 23:59SYD-ORD

29h 39m1 stop

13:49 - 09:00ORD-SYD

26h 11m1 stop

$1,830American Airlines

Find Deal

Mon, 17 Nov - Mon, 1 Dec

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets

Air New Zealand

8 Nov

SYD13:55Sydney Kingsford Smith

22h 35m

2 stops

ORD19:30Chicago O'Hare Intl

23 Nov

ORD14:30Chicago O'Hare Intl

25h 15m

2 stops

SYD08:45Sydney Kingsford Smith

$1,483

Find similar

Air New Zealand

3 Nov

SYD13:55Sydney Kingsford Smith

22h 35m

2 stops

ORD19:30Chicago O'Hare Intl

8 Nov

ORD13:00Chicago O'Hare Intl

26h 45m

2 stops

SYD08:45Sydney Kingsford Smith

$1,593

Find similar

Air New Zealand

13 Nov

SYD13:55Sydney Kingsford Smith

22h 35m

2 stops

ORD19:30Chicago O'Hare Intl

14 Nov

ORD14:35Chicago O'Hare Intl

25h 10m

2 stops

SYD08:45Sydney Kingsford Smith

$1,597

Find similar

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

American Airlines

18 Nov

SYD11:20Sydney Kingsford Smith

25h 20m

2 stops

ORD19:40Chicago O'Hare Intl

29 Nov

ORD21:42Chicago O'Hare Intl

42h 18m

1 stop

SYD09:00Sydney Kingsford Smith

$1,816

Find similar

American Airlines

17 Nov

SYD11:20Sydney Kingsford Smith

29h 39m

1 stop

ORD23:59Chicago O'Hare Intl

1 Dec

ORD13:49Chicago O'Hare Intl

26h 11m

1 stop

SYD09:00Sydney Kingsford Smith

$1,830

Find similar

American Airlines

3 Dec

SYD11:20Sydney Kingsford Smith

23h 32m

1 stop

ORD17:52Chicago O'Hare Intl

9 Dec

ORD18:17Chicago O'Hare Intl

21h 43m

1 stop

SYD09:00Sydney Kingsford Smith

$1,834

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

13:55-19:30

2 stops22h 35m

Chicago O'Hare Intl

Sun 23/11

14:30-08:45

2 stops25h 15m

$1,483

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 3/11

13:55-19:30

2 stops22h 35m

Chicago O'Hare Intl

Sat 8/11

13:00-08:45

2 stops26h 45m

$1,593

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/11

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 27/11

15:40-09:35

1 stop24h 55m

$1,665

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 13/11

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Fri 14/11

18:03-09:00

1 stop21h 57m

$1,703

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/12

11:20-16:08

1 stop21h 48m

Chicago O'Hare Intl

Tue 9/12

08:50-09:00

1 stop31h 10m

$1,736

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 17/11

11:20-21:24

1 stop27h 04m

Chicago O'Hare Intl

Mon 1/12

11:40-09:00

1 stop28h 20m

$1,739

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

17:45-23:00

1 stop22h 15m

Chicago O'Hare Intl

Sun 23/11

20:18-07:25

1 stop42h 07m

$1,763

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 18/11

11:20-19:40

2 stops25h 20m

Chicago O'Hare Intl

Sat 29/11

21:42-09:00

1 stop42h 18m

$1,816

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/11

11:20-20:00

2 stops25h 40m

Chicago O'Hare Intl

Thu 27/11

10:38-09:35

2 stops29h 57m

$1,824

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 17/11

11:20-23:59

1 stop29h 39m

Chicago O'Hare Intl

Mon 1/12

13:49-09:00

1 stop26h 11m

$1,830

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Sydney to Chicago

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

Prices

Airlines

Stopovers

What is the typical price of a round-trip flight between Sydney and Chicago?

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in March, then you should wait until May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,137.

What is the cheapest day to depart on your flight to Chicago?

Our data shows that Tuesday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $1,728. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $2,034. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Sydney to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as $1,725. Flights in the morning are often more expensive, with an average ticket price of $1,908.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Sydney when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,502 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sydney for as low as $1,194 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 56% on your flight if you consider stops on a Sydney to Chicago flight.

How have Sydney to Chicago flight prices changed over time?

As of October 2025, prices for Sydney to Chicago flights are approximately 60% cheaper when compared to flights at the same time last year.

When to book flights from Sydney to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated return price

Cheap Sydney to Chicago (SYD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago

Direct flights	None

There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.

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How far is Sydney Kingsford Smith to Chicago by plane?
There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 07m is a normal flight duration for this route.
When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago?
Prices for flights from Sydney Kingsford Smith Airport to Chicago were last updated today.
How many operators does momondo search for flights from Sydney Kingsford Smith Airport to Chicago?
The number of operators available for flights from Sydney Kingsford Smith Airport to Chicago is 6 as of October 2025.
How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago?
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 Sydney Kingsford Smith Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Sydney to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Sydney to Chicago is Qantas Airways (58% of total bookings). The next most popular airlines are Air Canada (17%), United Airlines (10%), and ANA (5%).

Best airlines flying from Sydney to Chicago

Compare and see reviews for airlines that fly from Sydney to Chicago with momondo

Airline	Rating	Free cancellation	Price
Qantas Airways	PriceFrom $1,012	Free cancellation	Rating 7.5 922 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,200	Free cancellation	Rating 7.2 11,026 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,214	Free cancellation	Rating 7.1 10,334 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,456	Free cancellation	Rating 8.0 516 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,617	Free cancellation	Rating 8.4 990 reviews	Search ANA flights
United Airlines	PriceFrom $1,669	Free cancellation	Rating 7.4 8,991 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Sydney to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Sydney to Chicago . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Sydney to Chicago with flexible booking policies on momondo?

Flights from Sydney to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Sydney to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Sydney to Chicago.

I’m not ready to book a flight from Sydney to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Sydney and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

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Cheap flights from Sydney to Chicago from $883

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 28/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Sydney to Chicago

Cheap return flights

Cheap one-way flights

Cheap last-minute flights

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

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Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

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How to get the cheapest flight ticket from Sydney to Chicago

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 Sydney and Chicago?

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in March, then you should wait until May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,137.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Sydney to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as $1,725. Flights in the morning are often more expensive, with an average ticket price of $1,908.

How far in advance should I book a flight to Chicago?

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 56% on your flight if you consider stops on a Sydney to Chicago flight.

How have Sydney to Chicago flight prices changed over time?

As of October 2025, prices for Sydney to Chicago flights are approximately 60% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Sydney Kingsford Smith to Chicago?

Etihad Airways, Air New Zealand, and Air Canada are the most popular carriers operating from Sydney Kingsford Smith to Chicago

Which airlines fly to Chicago?

Which airport is the most popular for stopovers for flights between Sydney and Chicago?

Los Angeles (LAX) was the most common stop: 64% of momondo users choosing one-stop flights on this route connected there.

Which stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Los Angeles (LAX) offer the lowest average return price of $1,205.

Which stopover airport has the shortest travel time from Sydney to Chicago?

Flights connecting via Vancouver (YVR) have the shortest average one-way travel time: 20h 21m.

Which stopover airport has the shortest connection time from Sydney to Chicago?

Dallas (DFW) has the shortest average stopover time for this route: 2h 10m.

When to book flights from Sydney to Chicago

Cheap Sydney to Chicago (SYD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago

Direct flights

How far is Sydney Kingsford Smith to Chicago by plane?

When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago?

How many operators does momondo search for flights from Sydney Kingsford Smith Airport to Chicago?

How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular airline from Sydney to Chicago?

Best airlines flying from Sydney to Chicago

Compare and see reviews for airlines that fly from Sydney to Chicago with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Sydney to Chicago?

Can I find flights from Sydney to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Sydney to Chicago?

I’m not ready to book a flight from Sydney to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago