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 40% 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.

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

Air New Zealand and Etihad Airways 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 stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Houston (IAH) offer the lowest average return price of $1,553.

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

Los Angeles (LAX) was the most common stop: 43% of momondo users choosing one-stop flights on this route connected there.

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 July 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.

$996 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 low for flights on this route. Typical prices usually range from $1,554 to $2,382. The lowest price recently found on this route was $1,287.

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.

06:05 - 06:17

SYD

ORD

39h 12m

2 stops

09:20 - 11:50

ORD

SYD

35h 30m

3 stops

$1,287Multiple Airlines

Wed, 12 Aug - Wed, 19 Aug

06:05 - 06:17

SYD

ORD

39h 12m

2 stops

09:20 - 11:50

ORD

SYD

35h 30m

3 stops

$1,292Multiple Airlines

Wed, 12 Aug - Wed, 19 Aug

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

09:20 - 11:50

ORD

SYD

35h 30m

3 stops

$1,307Multiple Airlines

Tue, 11 Aug - Tue, 18 Aug

09:10 - 18:01

SYD

ORD

23h 51m

2 stops

15:54 - 07:05

ORD

SYD

24h 11m

2 stops

$1,399American Airlines

Wed, 5 Aug - Thu, 20 Aug

09:10 - 15:54

SYD

ORD

21h 44m

1 stop

19:00 - 07:05

ORD

SYD

21h 05m

1 stop

$1,403American Airlines

Thu, 13 Aug - Thu, 20 Aug

09:10 - 14:54

SYD

ORD

20h 44m

1 stop

09:00 - 07:05

ORD

SYD

31h 05m

1 stop

$1,449American Airlines

Thu, 6 Aug - Mon, 10 Aug

09:10 - 16:49

SYD

ORD

22h 39m

1 stop

18:55 - 09:00

ORD

SYD

21h 05m

1 stop

$1,453American Airlines

Thu, 1 Oct - Tue, 24 Nov

10:15 - 16:39

SYD

MDW

22h 24m

2 stops

13:00 - 07:50

MDW

SYD

26h 50m

2 stops

$2,433Delta

Mon, 12 Oct - Tue, 20 Oct

09:15 - 18:19

SYD

MDW

24h 04m

2 stops

13:28 - 07:50

MDW

SYD

26h 22m

2 stops

$2,446Delta

Wed, 30 Sep - Tue, 13 Oct

10:40 - 22:10

SYD

MDW

28h 30m

2 stops

13:00 - 08:30

MDW

SYD

26h 30m

2 stops

$2,469Delta

Tue, 8 Dec - Thu, 14 Jan

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American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

American Airlines

18 July

SYD09:10Sydney Kingsford Smith

21h 50m

1 stop

ORD16:00Chicago O'Hare Intl

1 Aug

ORD08:10Chicago O'Hare Intl

31h 55m

1 stop

SYD07:05Sydney Kingsford Smith

$1,346

American Airlines

5 Aug

SYD09:10Sydney Kingsford Smith

23h 51m

2 stops

ORD18:01Chicago O'Hare Intl

20 Aug

ORD15:54Chicago O'Hare Intl

24h 11m

2 stops

SYD07:05Sydney Kingsford Smith

$1,399

American Airlines

13 Aug

SYD09:10Sydney Kingsford Smith

21h 44m

1 stop

ORD15:54Chicago O'Hare Intl

20 Aug

ORD19:00Chicago O'Hare Intl

21h 05m

1 stop

SYD07:05Sydney Kingsford Smith

$1,403

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

1 Oct

SYD09:10Sydney Kingsford Smith

21h 43m

1 stop

ORD15:53Chicago O'Hare Intl

20 Oct

ORD13:50Chicago O'Hare Intl

26h 15m

1 stop

SYD08:05Sydney Kingsford Smith

$1,524

Qantas Airways

24 Aug

SYD06:25Sydney Kingsford Smith

24h 29m

2 stops

ORD15:54Chicago O'Hare Intl

31 Aug

ORD21:06Chicago O'Hare Intl

56h 24m

2 stops

SYD20:30Sydney Kingsford Smith

$1,709

Qantas Airways

27 July

SYD06:25Sydney Kingsford Smith

28h 43m

2 stops

ORD20:08Chicago O'Hare Intl

12 Aug

ORD15:54Chicago O'Hare Intl

25h 21m

2 stops

SYD08:15Sydney Kingsford Smith

$1,804

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/8

06:05-06:17

2 stops39h 12m

Chicago O'Hare Intl

Wed 19/8

09:20-11:50

3 stops35h 30m

$1,287

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/8

06:05-06:17

2 stops39h 12m

Chicago O'Hare Intl

Wed 19/8

09:20-11:50

3 stops35h 30m

$1,292

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 11/8

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Tue 18/8

09:20-11:50

3 stops35h 30m

$1,307

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 5/8

09:10-18:01

2 stops23h 51m

Chicago O'Hare Intl

Thu 20/8

15:54-07:05

2 stops24h 11m

$1,399

Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 13/8

09:10-15:54

1 stop21h 44m

Chicago O'Hare Intl

Thu 20/8

19:00-07:05

1 stop21h 05m

$1,403

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 6/8

09:10-14:54

1 stop20h 44m

Chicago O'Hare Intl

Mon 10/8

09:00-07:05

1 stop31h 05m

$1,449

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:10-16:49

1 stop22h 39m

Chicago O'Hare Intl

Tue 24/11

18:55-09:00

1 stop21h 05m

$1,453

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 12/10

10:15-16:39

2 stops22h 24m

Chicago Midway

Tue 20/10

13:00-07:50

2 stops26h 50m

$2,433

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 30/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 13/10

13:28-07:50

2 stops26h 22m

$2,446

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 8/12

10:40-22:10

2 stops28h 30m

Chicago Midway

Thu 14/1

13:00-08:30

2 stops26h 30m

$2,469

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 December, then you should wait until August to fly from Sydney, when ticket prices are also cheap, with an average price of $896.

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 $1,955 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 $1,467 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 9% 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 July 2026, prices for Sydney to Chicago flights are approximately 73% 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	20h 10m
Direct flights	None

The fastest flight from Sydney to Chicago takes 20h 10m

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

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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 10m 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 July 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 (27% of total bookings). The next most popular airlines are Air Canada (24%), United Airlines (23%), and Air New Zealand (11%).

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 $1,082	Free cancellation	Rating 7.1 11,350 reviews	Search Air Canada flights
Qantas Airways	PriceFrom $1,261	Free cancellation	Rating 7.5 1,062 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,262	Free cancellation	Rating 7.1 11,822 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,413	Free cancellation	Rating 7.4 10,002 reviews	Search United Airlines flights
Air New Zealand	PriceFrom $1,422	Free cancellation	Rating 8.0 654 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,527	Free cancellation	Rating 8.3 1,271 reviews	Search ANA 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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Cheap flights from Sydney to Chicago from $996

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 12/8. 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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American Airlines flights from Sydney to Chicago

Our best American Airlines 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

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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?

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

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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