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

Flights via Vancouver (YVR) offer the lowest average return price of $1,209.

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.

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

Los Angeles (LAX) was the most common stop: 77% 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?

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

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 7 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 7 as of January 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.

$864 Cheap Flights from Sydney to Chicago in 2026

Q: 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 $1,113 to $1,928. The lowest price recently found on this route was $1,509.

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11:45 - 20:05

SYD

ORD

25h 20m2 stops

14:33 - 08:45

ORD

SYD

25h 12m2 stops

$1,509Air New Zealand

Thu, 29 Jan - Sun, 15 Feb

11:20 - 16:42

SYD

ORD

22h 22m1 stop

13:05 - 09:35

ORD

SYD

27h 30m1 stop

$1,526Air Canada

Tue, 27 Jan - Wed, 11 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

20:40 - 09:35

ORD

SYD

43h 55m2 stops

$1,538Air Canada

Thu, 29 Jan - Sun, 15 Feb

11:20 - 19:45

SYD

ORD

25h 25m2 stops

13:13 - 09:35

ORD

SYD

27h 22m2 stops

$1,550Air Canada

Tue, 27 Jan - Wed, 11 Feb

11:20 - 11:06

SYD

ORD

40h 46m2 stops

07:15 - 09:35

ORD

SYD

33h 20m2 stops

$1,572Air Canada

Mon, 26 Jan - Tue, 10 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

07:15 - 09:35

ORD

SYD

33h 20m2 stops

$1,573Air Canada

Mon, 26 Jan - Tue, 10 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

15:35 - 09:35

ORD

SYD

25h 00m1 stop

$1,591Air Canada

Thu, 29 Jan - Sun, 15 Feb

11:45 - 21:28

SYD

ORD

26h 43m2 stops

14:35 - 08:45

ORD

SYD

25h 10m2 stops

$1,599Air New Zealand

Fri, 20 Feb - Fri, 27 Feb

10:40 - 17:29

SYD

MDW

23h 49m2 stops

12:46 - 08:30

MDW

SYD

26h 44m2 stops

$1,728Delta

Mon, 26 Jan - Tue, 10 Feb

09:40 - 16:55

SYD

MDW

23h 15m2 stops

14:00 - 06:35

MDW

SYD

25h 35m2 stops

$1,802Delta

Thu, 19 Mar - Sat, 16 May

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

12 May

SYD09:55Sydney Kingsford Smith

26h 38m

2 stops

ORD21:33Chicago O'Hare Intl

15 May

ORD16:00Chicago O'Hare Intl

25h 45m

2 stops

SYD08:45Sydney Kingsford Smith

$1,432

Air New Zealand

26 Jan

SYD11:45Sydney Kingsford Smith

25h 20m

2 stops

ORD20:05Chicago O'Hare Intl

10 Feb

ORD14:40Chicago O'Hare Intl

26h 50m

2 stops

SYD10:30Sydney Kingsford Smith

$1,501

Air New Zealand

29 Jan

SYD11:45Sydney Kingsford Smith

25h 20m

2 stops

ORD20:05Chicago O'Hare Intl

15 Feb

ORD14:33Chicago O'Hare Intl

25h 12m

2 stops

SYD08:45Sydney Kingsford Smith

$1,509

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

28 Jan

SYD11:20Sydney Kingsford Smith

20h 37m

1 stop

ORD14:57Chicago O'Hare Intl

12 Feb

ORD20:45Chicago O'Hare Intl

43h 15m

1 stop

SYD09:00Sydney Kingsford Smith

$1,643

Qantas Airways

18 Apr

SYD09:10Sydney Kingsford Smith

20h 06m

1 stop

ORD14:16Chicago O'Hare Intl

3 May

ORD19:17Chicago O'Hare Intl

20h 48m

1 stop

SYD07:05Sydney Kingsford Smith

$1,928

Qantas Airways

16 Jan

SYD07:05Sydney Kingsford Smith

25h 32m

2 stops

ORD15:37Chicago O'Hare Intl

23 Jan

ORD14:15Chicago O'Hare Intl

26h 35m

2 stops

SYD09:50Sydney Kingsford Smith

$2,157

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

11:45-20:05

2 stops25h 20m

Chicago O'Hare Intl

Sun 15/2

14:33-08:45

2 stops25h 12m

$1,509

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 27/1

11:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Wed 11/2

13:05-09:35

1 stop27h 30m

$1,526

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Sun 15/2

20:40-09:35

2 stops43h 55m

$1,538

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 27/1

11:20-19:45

2 stops25h 25m

Chicago O'Hare Intl

Wed 11/2

13:13-09:35

2 stops27h 22m

$1,550

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 26/1

11:20-11:06

2 stops40h 46m

Chicago O'Hare Intl

Tue 10/2

07:15-09:35

2 stops33h 20m

$1,572

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 26/1

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 10/2

07:15-09:35

2 stops33h 20m

$1,573

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Sun 15/2

15:35-09:35

1 stop25h 00m

$1,591

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 20/2

11:45-21:28

2 stops26h 43m

Chicago O'Hare Intl

Fri 27/2

14:35-08:45

2 stops25h 10m

$1,599

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 26/1

10:40-17:29

2 stops23h 49m

Chicago Midway

Tue 10/2

12:46-08:30

2 stops26h 44m

$1,728

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-16:55

2 stops23h 15m

Chicago Midway

Sat 16/5

14:00-06:35

2 stops25h 35m

$1,802

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 $1,100.

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 $1,413 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 $1,131 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 65% 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 January 2026, prices for Sydney to Chicago flights are approximately 14% 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 31m
Direct flights	None

The fastest flight from Sydney to Chicago takes 19h 31m

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 31m 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 7 as of January 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 (59% of total bookings). The next most popular airlines are Air Canada (16%), United Airlines (11%), and Air New Zealand (6%).

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 $971	Free cancellation	Rating 7.5 967 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,158	Free cancellation	Rating 7.2 11,097 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,160	Free cancellation	Rating 7.1 10,603 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,404	Free cancellation	Rating 8.0 567 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,468	Free cancellation	Rating 7.4 9,139 reviews	Search United Airlines flights
ANA	PriceFrom $1,559	Free cancellation	Rating 8.4 1,060 reviews	Search ANA flights
Virgin Australia	PriceFrom $1,710	Free cancellation	Rating 7.6 430 reviews	Search Virgin Australia 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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Cheap flights from Sydney to Chicago from $864

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 18/4. 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

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Filter for what you want

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Find the cheapest flights from Sydney to Chicago

Cheap return flights

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Air New Zealand flights from Sydney to Chicago

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

Qantas Airways flights from Sydney to Chicago

Our best Qantas 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?

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 $1,100.

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 65% 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 January 2026, prices for Sydney to Chicago flights are approximately 14% 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 Delta 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: 77% 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 $1,209.

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