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

Houston (IAH) has the shortest average stopover time for this route: 1h 31m.

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: 19h 51m.

Which airlines fly to Chicago?

Qantas Airways, Air Canada and Air New Zealand 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 42% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Flights via Houston (IAH) offer the lowest average return price of $1,545.

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

Los Angeles (LAX) was the most common stop: 45% of momondo users choosing one-stop flights on this route connected there.

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

Etihad Airways and Delta 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 5 as of August 2026.

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.

$708 Cheap Flights from Sydney to Chicago in 2026

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Find the cheapest flights from Sydney to Chicago

Return

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

06:15 - 06:17

SYD

ORD

39h 02m

2 stops

06:20 - 22:25

ORD

SYD

49h 05m

3 stops

$1,163Multiple Airlines

Tue, 8 Sep - Tue, 22 Sep

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

06:30 - 22:25

ORD

SYD

48h 55m

3 stops

$1,187Multiple Airlines

Tue, 8 Sep - Tue, 22 Sep

09:20 - 10:15

SYD

ORD

39h 55m

2 stops

15:40 - 07:20

ORD

SYD

24h 40m

1 stop

$1,309Air Canada

Mon, 14 Sep - Mon, 28 Sep

09:20 - 14:43

SYD

ORD

20h 23m

1 stop

15:40 - 07:20

ORD

SYD

24h 40m

1 stop

$1,311Air Canada

Tue, 8 Sep - Tue, 22 Sep

11:55 - 00:59

SYD

ORD

28h 04m

2 stops

16:25 - 08:45

ORD

SYD

25h 20m

2 stops

$1,659Air New Zealand

Tue, 25 Aug - Tue, 1 Sep

09:55 - 00:59

SYD

ORD

30h 04m

2 stops

16:25 - 08:45

ORD

SYD

25h 20m

2 stops

$1,747Air New Zealand

Tue, 18 Aug - Wed, 2 Sep

22:00 - 23:00

SYD

ORD

40h 00m

2 stops

15:54 - 08:15

ORD

SYD

25h 21m

2 stops

$1,885Qantas Airways

Fri, 21 Aug - Sat, 5 Sep

10:20 - 14:50

SYD

ORD

19h 30m

1 stop

15:50 - 08:00

ORD

SYD

24h 10m

1 stop

$2,147United Airlines

Thu, 24 Sep - Mon, 12 Oct

09:30 - 14:36

SYD

ORD

20h 06m

1 stop

18:25 - 07:55

ORD

SYD

21h 30m

1 stop

$2,147United Airlines

Tue, 22 Sep - Mon, 12 Oct

09:10 - 14:54

SYD

ORD

20h 44m

1 stop

19:00 - 07:05

ORD

SYD

21h 05m

1 stop

$2,195Qantas Airways

Thu, 20 Aug - Fri, 4 Sep

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Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

14 Sept

SYD09:20Sydney Kingsford Smith

39h 55m

2 stops

ORD10:15Chicago O'Hare Intl

28 Sept

ORD15:40Chicago O'Hare Intl

24h 40m

1 stop

SYD07:20Sydney Kingsford Smith

$1,309

Air Canada

8 Sept

SYD09:20Sydney Kingsford Smith

20h 23m

1 stop

ORD14:43Chicago O'Hare Intl

22 Sept

ORD15:40Chicago O'Hare Intl

24h 40m

1 stop

SYD07:20Sydney Kingsford Smith

$1,311

Air Canada

8 Sept

SYD09:20Sydney Kingsford Smith

25h 52m

2 stops

ORD20:12Chicago O'Hare Intl

22 Sept

ORD08:45Chicago O'Hare Intl

31h 35m

2 stops

SYD07:20Sydney Kingsford Smith

$1,312

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

5 Aug

SYD07:50Sydney Kingsford Smith

31h 55m

2 stops

ORD00:45Chicago O'Hare Intl

20 Aug

ORD16:45Chicago O'Hare Intl

26h 55m

2 stops

SYD10:40Sydney Kingsford Smith

$1,663

Air New Zealand

4 Aug

SYD11:55Sydney Kingsford Smith

26h 21m

2 stops

ORD23:16Chicago O'Hare Intl

5 Aug

ORD14:15Chicago O'Hare Intl

27h 30m

2 stops

SYD08:45Sydney Kingsford Smith

$1,832

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 8/9

06:15-06:17

2 stops39h 02m

Chicago O'Hare Intl

Tue 22/9

06:20-22:25

3 stops49h 05m

$1,163

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 8/9

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Tue 22/9

06:30-22:25

3 stops48h 55m

$1,187

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 14/9

09:20-10:15

2 stops39h 55m

Chicago O'Hare Intl

Mon 28/9

15:40-07:20

1 stop24h 40m

$1,309

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:20-14:43

1 stop20h 23m

Chicago O'Hare Intl

Tue 22/9

15:40-07:20

1 stop24h 40m

$1,311

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 25/8

11:55-00:59

2 stops28h 04m

Chicago O'Hare Intl

Tue 1/9

16:25-08:45

2 stops25h 20m

$1,659

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 18/8

09:55-00:59

2 stops30h 04m

Chicago O'Hare Intl

Wed 2/9

16:25-08:45

2 stops25h 20m

$1,747

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 21/8

22:00-23:00

2 stops40h 00m

Chicago O'Hare Intl

Sat 5/9

15:54-08:15

2 stops25h 21m

$1,885

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 24/9

10:20-14:50

1 stop19h 30m

Chicago O'Hare Intl

Mon 12/10

15:50-08:00

1 stop24h 10m

$2,146

Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 22/9

09:30-14:36

1 stop20h 06m

Chicago O'Hare Intl

Mon 12/10

18:25-07:55

1 stop21h 30m

$2,146

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 20/8

09:10-14:54

1 stop20h 44m

Chicago O'Hare Intl

Fri 4/9

19:00-07:05

1 stop21h 05m

$2,195

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?

Prices are currently low for flights on this route.

Typical prices usually range from $1,348 to $1,874.
The lowest price recently found on this route was $1,163.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in September, then you should wait until October to fly from Sydney, when ticket prices are also cheap, with an average price of $1,518.

How far in advance should I book a flight from Sydney 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 $1,948 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 $1,460 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 17% 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 August 2026, prices for Sydney to Chicago flights are approximately 22% 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

Fastest flight time	23h 13m
Direct flights	None

The fastest flight from Sydney to Chicago takes 23h 13m

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

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Frequently asked questions about flying from Sydney to Chicago

How far is Sydney Kingsford Smith to Chicago by plane?
There are 14866.2 km between Sydney Kingsford Smith and Chicago. 23h 13m 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 5 as of August 2026.
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 (30% of total bookings). The next most popular airlines are Air Canada (24%), United Airlines (24%), and American Airlines (9%).

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
Air Canada	PriceFrom $1,077	Free cancellation	Rating 7.1 11,415 reviews	Search Air Canada flights
Qantas Airways	PriceFrom $1,254	Free cancellation	Rating 7.5 1,073 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,256	Free cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights
Air New Zealand	PriceFrom $1,345	Free cancellation	Rating 8.0 657 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,405	Free cancellation	Rating 7.4 10,062 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

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Fly into one of these airports located in Chicago

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Cheap flights from Sydney to Chicago from $698

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 18/11. 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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Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand 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.

See travel insights to Chicago from

How to get the cheapest flight ticket from Sydney to Chicago

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

What is the cheapest month to fly to Chicago?

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

Can stopping save me money on Sydney to Chicago flights?

How have Sydney to Chicago flight prices changed over time?

What is the cheapest airline that flies 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?

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

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

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

When to book flights from Sydney to Chicago

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

Fastest flight time

Direct flights

Frequently asked questions about flying 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?

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

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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