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

Los Angeles (LAX) was the most common stop: 47% 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 $1,376.

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?

Cathay Pacific is the most popular carrier operating from Sydney Kingsford Smith to Chicago

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 52% 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 October 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.

$713 Cheap Flights from Sydney to Chicago in 2026/27

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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.

11:20 - 14:37SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

20h 17m1 stop Vancouver Intl

10:33 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

30h 02m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$1,247Air Canada

Fri, 25 Dec - Thu, 31 Dec

11:20 - 19:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 10m2 stops Vancouver Intl Denver Intl

10:33 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

30h 02m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$1,250Air Canada

Fri, 25 Dec - Thu, 31 Dec

14:05 - 18:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 25m1 stop Dallas/Fort Worth

06:40 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 20m1 stop Los Angeles

$1,443Qantas Airways

Tue, 17 Nov - Tue, 24 Nov

11:30 - 16:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

46h 25m1 stop Manila Ninoy Aquino Intl

22:45 - 09:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 05m1 stop Manila Ninoy Aquino Intl

$1,445Philippine Airlines

Thu, 19 Nov - Wed, 25 Nov

11:30 - 16:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

46h 25m1 stop Manila Ninoy Aquino Intl

22:45 - 09:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 05m1 stop Manila Ninoy Aquino Intl

$1,459Philippine Airlines

Tue, 10 Nov - Wed, 25 Nov

11:10 - 00:13SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 03m1 stop Los Angeles

16:00 - 06:55ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 55m1 stop Dallas/Fort Worth

$1,470American Airlines

Thu, 26 Nov - Sat, 5 Dec

20:30 - 07:21SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

27h 51m1 stop Honolulu

06:40 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 20m1 stop Los Angeles

$1,593American Airlines

Thu, 19 Nov - Thu, 26 Nov

14:05 - 20:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 55m1 stop Dallas/Fort Worth

18:45 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 15m1 stop Los Angeles

$1,616Qantas Airways

Mon, 9 Nov - Tue, 24 Nov

10:40 - 20:15SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

26h 35m2 stops Los Angeles Detroit Metropolitan Wayne County

07:25 - 08:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

32h 05m2 stops Salt Lake City Los Angeles

$1,697Delta

Thu, 3 Dec - Sun, 13 Dec

10:40 - 20:15SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

26h 35m2 stops Los Angeles Detroit Metropolitan Wayne County

18:10 - 08:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 20m1 stop Los Angeles

$1,697Delta

Thu, 3 Dec - Sun, 13 Dec

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Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Cathay Pacific

29 Oct

SYD15:15Sydney Kingsford Smith

38h 15m

1 stop

ORD13:30Chicago O'Hare Intl

24 Nov

ORD14:10Chicago O'Hare Intl

29h 50m

1 stop

SYD13:00Sydney Kingsford Smith

$1,804

Cathay Pacific

19 Nov

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD12:30Chicago O'Hare Intl

22 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,832

Cathay Pacific

5 Nov

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD12:30Chicago O'Hare Intl

9 Nov

ORD14:10Chicago O'Hare Intl

37h 40m

1 stop

SYD20:50Sydney Kingsford Smith

$1,839

Turkish Airlines flights from Sydney to Chicago

Our best Turkish Airlines deals on Sydney to Chicago flight tickets

Turkish Airlines

5 Nov

SYD21:35Sydney Kingsford Smith

54h 25m

2 stops

ORD11:00Chicago O'Hare Intl

9 Nov

ORD20:15Chicago O'Hare Intl

54h 10m

2 stops

SYD19:25Sydney Kingsford Smith

$2,238

Turkish Airlines

5 Nov

SYD21:35Sydney Kingsford Smith

38h 45m

2 stops

ORD19:20Chicago O'Hare Intl

9 Nov

ORD20:15Chicago O'Hare Intl

54h 10m

2 stops

SYD19:25Sydney Kingsford Smith

$2,295

Turkish Airlines

5 Nov

SYD21:35Sydney Kingsford Smith

54h 25m

2 stops

ORD11:00Chicago O'Hare Intl

9 Nov

ORD20:15Chicago O'Hare Intl

54h 10m

2 stops

SYD19:25Sydney Kingsford Smith

$2,417

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

Fri 25/12

11:20-14:37

1 stop20h 17m

Chicago O'Hare Intl

Thu 31/12

10:33-09:35

2 stops30h 02m

$1,247

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 25/12

11:20-19:30

2 stops25h 10m

Chicago O'Hare Intl

Thu 31/12

10:33-09:35

2 stops30h 02m

$1,250

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 17/11

14:05-18:30

1 stop21h 25m

Chicago O'Hare Intl

Tue 24/11

06:40-09:00

1 stop33h 20m

$1,443

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 19/11

11:30-16:55

1 stop46h 25m

Chicago O'Hare Intl

Wed 25/11

22:45-09:50

1 stop42h 05m

$1,445

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 10/11

11:30-16:55

1 stop46h 25m

Chicago O'Hare Intl

Wed 25/11

22:45-09:50

1 stop42h 05m

$1,459

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 26/11

11:10-00:13

1 stop30h 03m

Chicago O'Hare Intl

Sat 5/12

16:00-06:55

1 stop21h 55m

$1,470

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 19/11

20:30-07:21

1 stop27h 51m

Chicago O'Hare Intl

Thu 26/11

06:40-09:00

1 stop33h 20m

$1,593

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 9/11

14:05-20:00

1 stop22h 55m

Chicago O'Hare Intl

Tue 24/11

18:45-09:00

1 stop21h 15m

$1,616

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/12

10:40-20:15

2 stops26h 35m

Chicago O'Hare Intl

Sun 13/12

07:25-08:30

2 stops32h 05m

$1,697

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/12

10:40-20:15

2 stops26h 35m

Chicago O'Hare Intl

Sun 13/12

18:10-08:30

1 stop21h 20m

$1,697

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 $1,371 to $2,070.
The lowest price recently found on this route was $1,247.

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 $1,633.

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 $2,096 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 $1,246 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 43% 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 2026, prices for Sydney to Chicago flights are approximately 79% 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	$713
Fastest flight time	20h 00m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $713. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,247.

The fastest flight from Sydney to Chicago takes 20h 00m

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. 20h 00m 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 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 (32% of total bookings). The next most popular airlines are United Airlines (21%), Air Canada (19%), and American Airlines (15%).

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 $953	Free cancellation	Rating 7.1 11,790 reviews	Search Air Canada flights
Delta	PriceFrom $1,053	Free cancellation	Rating 7.8 8,657 reviews	Search Delta flights
American Airlines	PriceFrom $1,067	Free cancellation	Rating 7.0 12,183 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,408	Free cancellation	Rating 7.3 10,396 reviews	Search United Airlines flights
Qantas Airways	PriceFrom $1,502	Free cancellation	Rating 7.5 1,115 reviews	Search Qantas Airways flights
Air New Zealand	PriceFrom $1,505	Free cancellation	Rating 8.0 675 reviews	Search Air New Zealand 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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Sydney to Chicago from $713

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 1/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Turkish Airlines flights from Sydney to Chicago

Our best Turkish Airlines 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

Fly to other destinations from Sydney

According to popular flight searches on momondo this year

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