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

Los Angeles (LAX) was the most common stop: 50% of momondo users choosing one-stop flights on this route connected there.

Which airlines fly to Chicago?

Qantas Airways, American Airlines and Air Canada 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 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 travel time from Sydney to Chicago?

Flights connecting via San Francisco (SFO) have the shortest average one-way travel time: 19h 30m.

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

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

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

Flights via Vancouver (YVR) offer the lowest average return price of $1,423.

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 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 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.

$747 Cheap Flights from Sydney to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Sydney to Chicago

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One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

11:20 - 14:32SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

20h 12m1 stop Vancouver Intl

13:55 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$1,433Air Canada

Thu, 21 Jan - Thu, 28 Jan

11:20 - 08:07SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

37h 47m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

08:40 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 55m2 stops Calgary Vancouver Intl

$1,434Air Canada

Thu, 4 Feb - Mon, 8 Feb

11:35 - 17:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

46h 20m1 stop Manila Ninoy Aquino Intl

23:45 - 09:45ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

43h 00m1 stop Manila Ninoy Aquino Intl

$1,954Philippine Airlines

Thu, 1 Apr - Mon, 10 May

08:45 - 12:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

44h 45m1 stop Hong Kong Intl

16:00 - 06:10ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

47h 10m1 stop Hong Kong Intl

$2,098Cathay Pacific

Thu, 18 Feb - Thu, 24 Jun

07:30 - 19:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

29h 25m2 stops Auckland Intl Houston George Bush Intcntl

17:58 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

45h 37m2 stops Houston George Bush Intcntl Auckland Intl

$2,959Air New Zealand

Tue, 1 Dec - Sun, 10 Jan

13:35 - 22:27SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 52m2 stops Los Angeles Salt Lake City

07:15 - 06:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

30h 35m2 stops Salt Lake City Los Angeles

$2,963Delta

Tue, 29 Dec - Tue, 5 Jan

13:35 - 22:14SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 39m1 stop Los Angeles

14:22 - 06:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

23h 28m1 stop Los Angeles

$2,963Delta

Tue, 29 Dec - Tue, 5 Jan

11:50 - 22:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

28h 09m2 stops Auckland Intl Los Angeles

18:29 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

45h 06m2 stops Houston George Bush Intcntl Auckland Intl

$3,144Air New Zealand

Fri, 18 Dec - Sat, 2 Jan

11:10 - 16:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 55m1 stop Los Angeles

15:30 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 30m1 stop Los Angeles

$3,148American Airlines

Mon, 21 Dec - Sun, 31 Jan

11:10 - 14:15SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

20h 05m1 stop Los Angeles

12:00 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 00m2 stops Atlanta Hartsfield-Jackson Los Angeles

$3,148American Airlines

Mon, 21 Dec - Mon, 1 Feb

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Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

21 Jan

SYD11:20Sydney Kingsford Smith

20h 12m

1 stop

ORD14:32Chicago O'Hare Intl

28 Jan

ORD13:55Chicago O'Hare Intl

26h 40m

2 stops

SYD09:35Sydney Kingsford Smith

$1,433

Air Canada

4 Feb

SYD11:20Sydney Kingsford Smith

37h 47m

2 stops

ORD08:07Chicago O'Hare Intl

8 Feb

ORD15:35Chicago O'Hare Intl

25h 00m

1 stop

SYD09:35Sydney Kingsford Smith

$1,434

Air Canada

21 Jan

SYD11:20Sydney Kingsford Smith

20h 12m

1 stop

ORD14:32Chicago O'Hare Intl

28 Jan

ORD15:35Chicago O'Hare Intl

25h 00m

1 stop

SYD09:35Sydney Kingsford Smith

$1,436

Qatar Airways flights from Sydney to Chicago

Our best Qatar Airways deals on Sydney to Chicago flight tickets

Qatar Airways

21 Nov

SYD22:10Sydney Kingsford Smith

33h 20m

1 stop

ORD14:30Chicago O'Hare Intl

23 Jan

ORD18:50Chicago O'Hare Intl

31h 30m

1 stop

SYD19:20Sydney Kingsford Smith

$2,487

Qatar Airways

22 Nov

SYD22:10Sydney Kingsford Smith

33h 20m

1 stop

ORD14:30Chicago O'Hare Intl

24 Jan

ORD18:50Chicago O'Hare Intl

31h 30m

1 stop

SYD19:20Sydney Kingsford Smith

$2,524

Qatar Airways

21 Nov

SYD22:10Sydney Kingsford Smith

33h 20m

1 stop

ORD14:30Chicago O'Hare Intl

24 Jan

ORD18:50Chicago O'Hare Intl

31h 30m

1 stop

SYD19:20Sydney Kingsford Smith

$2,567

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 21/1

11:20-14:32

1 stop20h 12m

Chicago O'Hare Intl

Thu 28/1

13:55-09:35

2 stops26h 40m

$1,433

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 4/2

11:20-08:07

2 stops37h 47m

Chicago O'Hare Intl

Mon 8/2

08:40-09:35

2 stops31h 55m

$1,434

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 1/4

11:35-17:55

1 stop46h 20m

Chicago O'Hare Intl

Mon 10/5

23:45-09:45

1 stop43h 00m

$1,954

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 18/2

08:45-12:30

1 stop44h 45m

Chicago O'Hare Intl

Thu 24/6

16:00-06:10

1 stop47h 10m

$2,098

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 1/12

07:30-19:55

2 stops29h 25m

Chicago O'Hare Intl

Sun 10/1

17:58-08:35

2 stops45h 37m

$2,958

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 29/12

13:35-22:27

2 stops25h 52m

Chicago O'Hare Intl

Tue 5/1

07:15-06:50

2 stops30h 35m

$2,963

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 29/12

13:35-22:14

1 stop25h 39m

Chicago O'Hare Intl

Tue 5/1

14:22-06:50

1 stop23h 28m

$2,963

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 18/12

11:50-22:59

2 stops28h 09m

Chicago O'Hare Intl

Sat 2/1

18:29-08:35

2 stops45h 06m

$3,144

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 21/12

11:10-16:05

1 stop21h 55m

Chicago O'Hare Intl

Sun 31/1

15:30-09:00

1 stop24h 30m

$3,148

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 21/12

11:10-14:15

1 stop20h 05m

Chicago O'Hare Intl

Mon 1/2

12:00-09:00

2 stops28h 00m

$3,148

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 typical for flights on this route.

Typical prices usually range from $1,171 to $2,065.
The lowest price recently found on this route was $1,433.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in October, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,689.

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 $2,177 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 $1,289 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 31% 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 2026, prices for Sydney to Chicago flights are approximately 40% 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

Best price found	$747
Fastest flight time	23h 50m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $747. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,433.

The fastest flight from Sydney to Chicago takes 23h 50m

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

Search flight deals

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 50m 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 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 United Airlines (23%), Air Canada (18%), and American Airlines (16%).

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 $986	Free cancellation	Rating 7.1 11,897 reviews	Search Air Canada flights
American Airlines	PriceFrom $987	Free cancellation	Rating 7.0 12,234 reviews	Search American Airlines flights
Delta	PriceFrom $1,089	Free cancellation	Rating 7.8 8,715 reviews	Search Delta flights
Air New Zealand	PriceFrom $1,392	Free cancellation	Rating 8.0 684 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,456	Free cancellation	Rating 7.3 10,495 reviews	Search United Airlines flights
Qantas Airways	PriceFrom $1,577	Free cancellation	Rating 7.5 1,125 reviews	Search Qantas Airways 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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Fly into one of these airports located in Chicago

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Chicago O'Hare Intl Airport

Cheap flights from Sydney to Chicago from $747

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 5/3. 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

Qatar Airways flights from Sydney to Chicago

Our best Qatar Airways deals on Sydney to Chicago flight tickets

momondo Fare Finder

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

Best price found

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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