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 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 offers the lowest fares from Sydney to Chicago?

Flights via Vancouver (YVR) offer the lowest average return price of $1,356.

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 and Delta are the most popular carriers operating from Sydney Kingsford Smith to Chicago

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.

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 September 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.

$182 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

Return

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

10:20 - 20:01SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 41m1 stop Vancouver Intl

10:37 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 58m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$1,300Air Canada

Wed, 28 Oct - Tue, 24 Nov

10:20 - 20:06SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 46m1 stop Vancouver Intl

15:40 - 08:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 40m1 stop Vancouver Intl

$1,303Air Canada

Mon, 5 Oct - Mon, 19 Oct

14:15 - 05:16SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

31h 01m3 stops Nadi Los Angeles Las Vegas Harry Reid Intl

06:30 - 12:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

38h 05m3 stops Denver Intl Los Angeles Nadi

$1,386Multiple Airlines

Thu, 22 Oct - Mon, 26 Oct

09:20 - 23:32SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

29h 12m3 stops Vancouver Intl Toronto Pearson Intl Washington, D.C. Dulles Intl

19:45 - 11:40ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

23h 55m2 stops Vancouver Intl Brisbane

$1,640Multiple Airlines

Thu, 1 Oct - Fri, 16 Oct

07:30 - 22:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

31h 29m2 stops Auckland Intl Los Angeles

14:00 - 12:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 50m2 stops Los Angeles Auckland Intl

$1,803Air New Zealand

Tue, 27 Oct - Wed, 11 Nov

11:10 - 05:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

35h 49m1 stop Los Angeles

15:06 - 06:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

22h 29m1 stop Las Vegas Harry Reid Intl

$2,132Qantas Airways

Tue, 1 Dec - Tue, 26 Jan

11:10 - 05:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

35h 49m1 stop Los Angeles

15:06 - 06:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

22h 29m1 stop Las Vegas Harry Reid Intl

$2,135Qantas Airways

Tue, 1 Dec - Tue, 26 Jan

11:15 - 05:02SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

34h 47m1 stop Los Angeles

07:56 - 06:25ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 29m1 stop San Francisco

$2,407American Airlines

Fri, 4 Dec - Fri, 25 Dec

11:15 - 05:02SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

34h 47m1 stop Los Angeles

07:56 - 06:25ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 29m1 stop San Francisco

$2,417American Airlines

Fri, 4 Dec - Fri, 25 Dec

14:05 - 21:46SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

24h 41m2 stops Auckland Intl Los Angeles

15:00 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 35m2 stops San Francisco Auckland Intl

$4,110Air New Zealand

Wed, 3 Mar - Sun, 7 Mar

Cheap last-minute flights

Enter your travel dates to find the best prices.

10:10 - 13:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

42h 45m1 stop Hong Kong Intl

16:15 - 20:10ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

36h 55m1 stop Hong Kong Intl

$2,390Cathay Pacific

Wed, 16 Sep - Sun, 20 Sep

09:20 - 17:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 45m2 stops Vancouver Intl Calgary

08:45 - 08:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 35m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$2,396Air Canada

Thu, 17 Sep - Wed, 14 Oct

09:20 - 16:45SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 25m1 stop Vancouver Intl

08:45 - 08:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 35m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$2,396Air Canada

Thu, 17 Sep - Wed, 14 Oct

14:05 - 13:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

38h 50m1 stop Hong Kong Intl

16:15 - 18:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

34h 45m2 stops Hong Kong Intl Melbourne

$2,442Multiple Airlines

Wed, 16 Sep - Sun, 20 Sep

19:45 - 13:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

33h 10m2 stops Perth Hong Kong Intl

16:15 - 16:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 35m2 stops Hong Kong Intl Melbourne

$2,489Multiple Airlines

Wed, 16 Sep - Sun, 20 Sep

17:50 - 00:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 40m2 stops Los Angeles Phoenix Sky Harbor Intl

15:20 - 08:05ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 45m2 stops San Francisco Los Angeles

$18,027American Airlines

Wed, 16 Sep - Sun, 4 Oct

17:50 - 15:53SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

37h 03m1 stop Los Angeles

18:02 - 06:55ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

20h 53m1 stop Dallas/Fort Worth

$18,449Qantas Airways

Sat, 19 Sep - Tue, 6 Oct

17:50 - 05:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

27h 09m1 stop Los Angeles

21:10 - 08:05ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 55m1 stop Los Angeles

$18,528American Airlines

Sat, 19 Sep - Sun, 4 Oct

09:30 - 17:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 35m2 stops Los Angeles Denver Intl

18:06 - 08:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 54m1 stop Los Angeles

$18,532United Airlines

Sat, 19 Sep - Mon, 5 Oct

10:20 - 20:28SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 08m1 stop San Francisco

16:40 - 06:55ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

23h 15m1 stop San Francisco

$18,532United Airlines

Thu, 17 Sep - Thu, 1 Oct

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Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

28 Oct

SYD10:20Sydney Kingsford Smith

25h 41m

1 stop

ORD20:01Chicago O'Hare Intl

24 Nov

ORD10:37Chicago O'Hare Intl

29h 58m

2 stops

SYD09:35Sydney Kingsford Smith

$1,300

Air Canada

5 Oct

SYD10:20Sydney Kingsford Smith

25h 46m

1 stop

ORD20:06Chicago O'Hare Intl

19 Oct

ORD15:40Chicago O'Hare Intl

24h 40m

1 stop

SYD08:20Sydney Kingsford Smith

$1,303

Air Canada

5 Oct

SYD10:20Sydney Kingsford Smith

20h 23m

1 stop

ORD14:43Chicago O'Hare Intl

19 Oct

ORD11:05Chicago O'Hare Intl

29h 15m

2 stops

SYD08:20Sydney Kingsford Smith

$1,306

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Cathay Pacific

16 Sept

SYD10:10Sydney Kingsford Smith

42h 45m

1 stop

ORD13:55Chicago O'Hare Intl

20 Sept

ORD16:15Chicago O'Hare Intl

36h 55m

1 stop

SYD20:10Sydney Kingsford Smith

$2,390

Cathay Pacific

17 Sept

SYD07:40Sydney Kingsford Smith

45h 15m

1 stop

ORD13:55Chicago O'Hare Intl

14 Oct

ORD16:15Chicago O'Hare Intl

28h 30m

1 stop

SYD12:45Sydney Kingsford Smith

$2,672

Cathay Pacific

25 Sept

SYD14:05Sydney Kingsford Smith

38h 50m

1 stop

ORD13:55Chicago O'Hare Intl

4 Oct

ORD16:15Chicago O'Hare Intl

28h 30m

1 stop

SYD12:45Sydney Kingsford Smith

$2,726

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

Wed 28/10

10:20-20:01

1 stop25h 41m

Chicago O'Hare Intl

Tue 24/11

10:37-09:35

2 stops29h 58m

$1,300

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 5/10

10:20-20:06

1 stop25h 46m

Chicago O'Hare Intl

Mon 19/10

15:40-08:20

1 stop24h 40m

$1,303

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 22/10

14:15-05:16

3 stops31h 01m

Chicago O'Hare Intl

Mon 26/10

06:30-12:35

3 stops38h 05m

$1,386

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:20-23:32

3 stops29h 12m

Chicago O'Hare Intl

Fri 16/10

19:45-11:40

2 stops23h 55m

$1,640

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 27/10

07:30-22:59

2 stops31h 29m

Chicago O'Hare Intl

Wed 11/11

14:00-12:50

2 stops29h 50m

$1,803

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 1/12

11:10-05:59

1 stop35h 49m

Chicago O'Hare Intl

Tue 26/1

15:06-06:35

1 stop22h 29m

$2,132

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 1/12

11:10-05:59

1 stop35h 49m

Chicago O'Hare Intl

Tue 26/1

15:06-06:35

1 stop22h 29m

$2,135

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 4/12

11:15-05:02

1 stop34h 47m

Chicago O'Hare Intl

Fri 25/12

07:56-06:25

1 stop29h 29m

$2,407

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 4/12

11:15-05:02

1 stop34h 47m

Chicago O'Hare Intl

Fri 25/12

07:56-06:25

1 stop29h 29m

$2,417

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 3/3

14:05-21:46

2 stops24h 41m

Chicago O'Hare Intl

Sun 7/3

15:00-08:35

2 stops24h 35m

$4,110

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 $1,362 to $2,253.
The lowest price recently found on this route was $1,300.

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 $1,603.

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 $2,012 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 $1,227 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 September 2026, prices for Sydney to Chicago flights are approximately 1% more expensive 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	$182
Fastest flight time	22h 34m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $182. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,300.

The fastest flight from Sydney to Chicago takes 22h 34m

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. 22h 34m 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 September 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 (31% of total bookings). The next most popular airlines are United Airlines (23%), Air Canada (22%), and American Airlines (12%).

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 $939	Free cancellation	Rating 7.1 11,635 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,327	Free cancellation	Rating 8.0 669 reviews	Search Air New Zealand flights
American Airlines	PriceFrom $1,329	Free cancellation	Rating 7.1 12,062 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,387	Free cancellation	Rating 7.4 10,215 reviews	Search United Airlines flights
Qantas Airways	PriceFrom $1,393	Free cancellation	Rating 7.5 1,098 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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Complete your trip

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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 $182

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 22/10. 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

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific 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

Complete your trip to Chicago

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According to popular flight searches on momondo this year