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

Houston (IAH) has the shortest average stopover time for this route: 1h 43m.

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

Flights via Los Angeles (LAX) offer the lowest average return price of $1,198.

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.

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

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

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

Los Angeles (LAX) was the most common stop: 63% 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 Houston (IAH) have the shortest average one-way travel time: 20h 04m.

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 November 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.

$936 Cheap Flights from Sydney to Chicago in 2025/26

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09:55 - 18:52SYD-ORD

25h 57m2 stops

13:00 - 08:45ORD-SYD

26h 45m2 stops

$1,495Air New Zealand

Find Deal

Mon, 2 Feb - Sun, 8 Feb

11:20 - 16:08SYD-ORD

21h 48m1 stop

11:45 - 09:00ORD-SYD

28h 15m1 stop

$1,559American Airlines

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Mon, 1 Dec - Tue, 16 Dec

21:45 - 07:20SYD-ORD

26h 35m1 stop

07:15 - 19:15ORD-SYD

45h 00m2 stops

$1,646ANA

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Thu, 12 Feb - Wed, 6 May

12:25 - 05:01SYD-ORD

33h 36m2 stops

16:25 - 20:15ORD-SYD

34h 50m1 stop

$1,718ANA

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Thu, 19 Feb - Mon, 2 Mar

11:45 - 19:51SYD-ORD

25h 06m2 stops

16:05 - 08:45ORD-SYD

25h 40m2 stops

$1,773Air New Zealand

Find Deal

Sun, 1 Feb - Sat, 9 May

11:20 - 14:41SYD-ORD

20h 21m1 stop

20:15 - 09:35ORD-SYD

44h 20m2 stops

$1,827Air Canada

Find Deal

Mon, 2 Feb - Sun, 8 Feb

11:20 - 19:30SYD-ORD

25h 10m2 stops

10:00 - 09:35ORD-SYD

30h 35m2 stops

$1,864Air Canada

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Thu, 19 Feb - Mon, 2 Mar

10:40 - 17:32SYD-MDW

23h 52m2 stops

12:46 - 08:30MDW-SYD

26h 44m2 stops

$2,147Delta

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Mon, 2 Feb - Thu, 19 Feb

14:15 - 22:44SYD-MDW

25h 29m2 stops

09:34 - 08:30MDW-SYD

29h 56m2 stops

$2,297Delta

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Thu, 19 Feb - Mon, 2 Mar

06:20 - 20:45SYD-MDW

31h 25m2 stops

08:00 - 06:55MDW-SYD

29h 55m1 stop

$4,101Multiple Airlines

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Fri, 26 Dec - Fri, 2 Jan

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets

ANA

12 Feb

SYD21:45Sydney Kingsford Smith

26h 35m

1 stop

ORD07:20Chicago O'Hare Intl

6 May

ORD07:15Chicago O'Hare Intl

45h 00m

2 stops

SYD19:15Sydney Kingsford Smith

$1,646

Find similar

ANA

19 Feb

SYD12:25Sydney Kingsford Smith

33h 36m

2 stops

ORD05:01Chicago O'Hare Intl

2 Mar

ORD16:25Chicago O'Hare Intl

34h 50m

1 stop

SYD20:15Sydney Kingsford Smith

$1,718

Find similar

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

2 Feb

SYD11:20Sydney Kingsford Smith

20h 21m

1 stop

ORD14:41Chicago O'Hare Intl

8 Feb

ORD20:15Chicago O'Hare Intl

44h 20m

2 stops

SYD09:35Sydney Kingsford Smith

$1,827

Find similar

Air Canada

19 Feb

SYD11:20Sydney Kingsford Smith

25h 10m

2 stops

ORD19:30Chicago O'Hare Intl

2 Mar

ORD10:00Chicago O'Hare Intl

30h 35m

2 stops

SYD09:35Sydney Kingsford Smith

$1,864

Find similar

Air Canada

2 Feb

SYD11:20Sydney Kingsford Smith

20h 21m

1 stop

ORD14:41Chicago O'Hare Intl

19 Feb

ORD10:00Chicago O'Hare Intl

30h 35m

2 stops

SYD09:35Sydney Kingsford Smith

$1,870

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

09:55-18:52

2 stops25h 57m

Chicago O'Hare Intl

Sun 8/2

13:00-08:45

2 stops26h 45m

$1,495

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 1/12

11:20-16:08

1 stop21h 48m

Chicago O'Hare Intl

Tue 16/12

11:45-09:00

1 stop28h 15m

$1,559

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 12/2

21:45-07:20

1 stop26h 35m

Chicago O'Hare Intl

Wed 6/5

07:15-19:15

2 stops45h 00m

$1,646

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

12:25-05:01

2 stops33h 36m

Chicago O'Hare Intl

Mon 2/3

16:25-20:15

1 stop34h 50m

$1,718

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 1/2

11:45-19:51

2 stops25h 06m

Chicago O'Hare Intl

Sat 9/5

16:05-08:45

2 stops25h 40m

$1,773

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Sun 8/2

20:15-09:35

2 stops44h 20m

$1,827

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

11:20-19:30

2 stops25h 10m

Chicago O'Hare Intl

Mon 2/3

10:00-09:35

2 stops30h 35m

$1,864

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40-17:32

2 stops23h 52m

Chicago Midway

Thu 19/2

12:46-08:30

2 stops26h 44m

$2,147

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/2

14:15-22:44

2 stops25h 29m

Chicago Midway

Mon 2/3

09:34-08:30

2 stops29h 56m

$2,297

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

06:20-20:45

2 stops31h 25m

Chicago Midway

Fri 2/1

08:00-06:55

1 stop29h 55m

$4,101

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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 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 $1,132.

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 $1,718. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $2,023. 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 $1,715. Flights in the morning are often more expensive, with an average ticket price of $1,897.

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 $1,491 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 $1,187 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 November 2025, prices for Sydney to Chicago flights are approximately 44% 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 November 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 (59% of total bookings). The next most popular airlines are Air Canada (16%), 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 $1,006	Free cancellation	Rating 7.5 933 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,193	Free cancellation	Rating 7.2 11,049 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,196	Free cancellation	Rating 7.1 10,443 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,523	Free cancellation	Rating 8.0 526 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,607	Free cancellation	Rating 8.4 1,003 reviews	Search ANA flights
United Airlines	PriceFrom $1,660	Free cancellation	Rating 7.4 9,015 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 $936

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 26/11. 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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Big names, great deals

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Find the cheapest flights from Sydney to Chicago

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ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

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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 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 $1,132.

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 $1,715. Flights in the morning are often more expensive, with an average ticket price of $1,897.

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 November 2025, prices for Sydney to Chicago flights are approximately 44% cheaper when compared to flights at the same time last year.

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

Air New Zealand, Air Canada, and Qantas Airways 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: 63% 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 $1,198.

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

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 20h 04m.

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

Houston (IAH) has the shortest average stopover time for this route: 1h 43m.

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