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

Los Angeles (LAX) was the most common stop: 66% 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 Vancouver (YVR) offer the lowest average return price of $1,227.

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.

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

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

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 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.

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 December 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.

$937 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 $1,777 to $2,527. The lowest price recently found on this route was $1,611.

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13:55 - 23:14

SYD

ORD

26h 19m2 stops

15:53 - 15:55

ORD

SYD

31h 02m2 stops

$1,611Air New Zealand

Wed, 28 Jan - Wed, 4 Feb

11:20 - 14:04

SYD

ORD

19h 44m1 stop

20:55 - 09:00

ORD

SYD

43h 05m1 stop

$1,709Qantas Airways

Thu, 19 Feb - Fri, 6 Mar

11:20 - 17:36

SYD

ORD

23h 16m1 stop

17:30 - 07:05

ORD

SYD

22h 35m1 stop

$1,721American Airlines

Tue, 3 Mar - Tue, 14 Apr

11:20 - 16:38

SYD

ORD

22h 18m1 stop

17:02 - 07:05

ORD

SYD

23h 03m2 stops

$1,728American Airlines

Tue, 3 Mar - Tue, 14 Apr

14:05 - 18:46

SYD

ORD

21h 41m2 stops

17:02 - 07:05

ORD

SYD

23h 03m2 stops

$1,739American Airlines

Tue, 3 Mar - Tue, 14 Apr

11:55 - 21:31

SYD

ORD

24h 36m2 stops

16:40 - 08:45

ORD

SYD

25h 05m2 stops

$1,767Air New Zealand

Sat, 16 May - Sat, 6 Jun

11:55 - 23:28

SYD

ORD

26h 33m2 stops

16:40 - 08:45

ORD

SYD

25h 05m2 stops

$1,771Multiple Airlines

Sat, 16 May - Sat, 6 Jun

12:10 - 14:45

SYD

ORD

19h 35m1 stop

14:26 - 09:05

ORD

SYD

25h 39m2 stops

$1,810United Airlines

Thu, 19 Feb - Fri, 6 Mar

11:50 - 05:05

SYD

ORD

32h 15m2 stops

17:45 - 09:25

ORD

SYD

24h 40m1 stop

$1,832ANA

Thu, 11 Jun - Thu, 6 Aug

13:55 - 20:25

SYD

ORD

23h 30m2 stops

15:53 - 10:30

ORD

SYD

25h 37m2 stops

$1,861Air New Zealand

Thu, 29 Jan - Thu, 5 Feb

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Cathay Pacific

11 June

SYD14:05Sydney Kingsford Smith

39h 20m

1 stop

ORD14:25Chicago O'Hare Intl

6 Aug

ORD16:00Chicago O'Hare Intl

37h 10m

1 stop

SYD20:10Sydney Kingsford Smith

$2,013

Find similar

Cathay Pacific

28 Jan

SYD15:15Sydney Kingsford Smith

38h 40m

1 stop

ORD12:55Chicago O'Hare Intl

4 Feb

ORD14:35Chicago O'Hare Intl

28h 25m

1 stop

SYD12:00Sydney Kingsford Smith

$2,117

Find similar

Cathay Pacific

4 Mar

SYD11:05Sydney Kingsford Smith

42h 50m

1 stop

ORD12:55Chicago O'Hare Intl

8 Mar

ORD15:35Chicago O'Hare Intl

26h 00m

1 stop

SYD09:35Sydney Kingsford Smith

$2,185

Find similar

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

28 Jan

SYD13:55Sydney Kingsford Smith

26h 19m

2 stops

ORD23:14Chicago O'Hare Intl

4 Feb

ORD15:53Chicago O'Hare Intl

31h 02m

2 stops

SYD15:55Sydney Kingsford Smith

$1,611

Find similar

Air New Zealand

16 May

SYD11:55Sydney Kingsford Smith

24h 36m

2 stops

ORD21:31Chicago O'Hare Intl

6 June

ORD16:40Chicago O'Hare Intl

25h 05m

2 stops

SYD08:45Sydney Kingsford Smith

$1,767

Find similar

Air New Zealand

29 Jan

SYD13:55Sydney Kingsford Smith

23h 30m

2 stops

ORD20:25Chicago O'Hare Intl

5 Feb

ORD15:53Chicago O'Hare Intl

25h 37m

2 stops

SYD10:30Sydney Kingsford Smith

$1,861

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 28/1

13:55-23:14

2 stops26h 19m

Chicago O'Hare Intl

Wed 4/2

15:53-15:55

2 stops31h 02m

$1,611

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

11:20-14:04

1 stop19h 44m

Chicago O'Hare Intl

Fri 6/3

20:55-09:00

1 stop43h 05m

$1,709

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

11:20-17:36

1 stop23h 16m

Chicago O'Hare Intl

Tue 14/4

17:30-07:05

1 stop22h 35m

$1,721

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

11:20-16:38

1 stop22h 18m

Chicago O'Hare Intl

Tue 14/4

17:02-07:05

2 stops23h 03m

$1,728

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

14:05-18:46

2 stops21h 41m

Chicago O'Hare Intl

Tue 14/4

17:02-07:05

2 stops23h 03m

$1,739

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 16/5

11:55-21:31

2 stops24h 36m

Chicago O'Hare Intl

Sat 6/6

16:40-08:45

2 stops25h 05m

$1,767

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 16/5

11:55-23:28

2 stops26h 33m

Chicago O'Hare Intl

Sat 6/6

16:40-08:45

2 stops25h 05m

$1,771

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

12:10-14:45

1 stop19h 35m

Chicago O'Hare Intl

Fri 6/3

14:26-09:05

2 stops25h 39m

$1,810

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 11/6

11:50-05:05

2 stops32h 15m

Chicago O'Hare Intl

Thu 6/8

17:45-09:25

1 stop24h 40m

$1,832

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

13:55-20:25

2 stops23h 30m

Chicago O'Hare Intl

Thu 5/2

15:53-10:30

2 stops25h 37m

$1,861

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 February to fly from Sydney, when ticket prices are also cheap, with an average price of $1,111.

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 $1,692. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $1,992. 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 $1,689. Flights in the morning are often more expensive, with an average ticket price of $1,868.

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 $1,448 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 $1,163 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 59% 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 December 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

Fastest flight time	19h 44m
Direct flights	None

The fastest flight from Sydney to Chicago takes 19h 44m

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

Search flight deals

How far is Sydney Kingsford Smith to Chicago by plane?
There are 14866.2 km between Sydney Kingsford Smith and Chicago. 19h 44m 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 December 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 (61% of total bookings). The next most popular airlines are Air Canada (16%), United Airlines (9%), and Air New Zealand (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 $989	Free cancellation	Rating 7.5 946 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,175	Free cancellation	Rating 7.2 11,049 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,177	Free cancellation	Rating 7.1 10,531 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,426	Free cancellation	Rating 8.0 552 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,583	Free cancellation	Rating 8.4 1,025 reviews	Search ANA flights
United Airlines	PriceFrom $1,607	Free cancellation	Rating 7.4 9,094 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.

Start using Trips

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Find better results for your trip to the United States

Cheap flights from Sydney to Chicago from $937

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 10/2. 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

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Price Alerts

Find the cheapest flights from Sydney to Chicago

Cheap return flights

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Cheap last-minute flights

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific 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?

If you don’t want to visit Chicago in March, then you should wait until February to fly from Sydney, when ticket prices are also cheap, with an average price of $1,111.

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 $1,689. Flights in the morning are often more expensive, with an average ticket price of $1,868.

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 59% 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 December 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?

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: 66% 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 Vancouver (YVR) offer the lowest average return price of $1,227.

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

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

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

Fastest flight time

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