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 65% 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 Vancouver (YVR) have the shortest average one-way travel time: 20h 18m.

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

Flights via Los Angeles (LAX) offer the lowest average return price of $1,186.

Which stopover airport has the shortest connection time from Sydney to Chicago?

Dallas (DFW) has the shortest average stopover time for this route: 2h 10m.

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

Los Angeles (LAX) was the most common stop: 65% 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 Canada, Etihad Airways, and Cathay Pacific are the most popular carriers operating from Sydney Kingsford Smith to Chicago

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 September 2025.

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.

$638 Cheap Flights from Sydney to Chicago in 2025/26

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 $1,511 to $2,115. The lowest price recently found on this route was $1,303.

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Find the cheapest flights from Sydney to Chicago

Round-trip

One-way

Last minute

Cheap return flights

11:20 - 15:10SYD-ORD

44h 50m2 stops

15:40 - 09:35ORD-SYD

24h 55m1 stop

$1,303Air Canada

Find Deal

Sat, 8 Nov - Sat, 22 Nov

11:20 - 19:30SYD-ORD

25h 10m2 stops

08:00 - 09:35ORD-SYD

32h 35m2 stops

$1,316Air Canada

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Sat, 8 Nov - Sat, 22 Nov

10:20 - 08:00SYD-ORD

37h 40m2 stops

15:40 - 09:35ORD-SYD

24h 55m1 stop

$1,322Air Canada

Find Deal

Wed, 29 Oct - Wed, 5 Nov

10:20 - 14:41SYD-ORD

20h 21m1 stop

15:40 - 09:35ORD-SYD

24h 55m1 stop

$1,325Air Canada

Find Deal

Thu, 30 Oct - Thu, 6 Nov

09:10 - 15:51SYD-ORD

21h 41m1 stop

18:03 - 09:00ORD-SYD

21h 57m1 stop

$1,421Qantas Airways

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Tue, 30 Sep - Wed, 12 Nov

09:10 - 17:18SYD-ORD

23h 08m2 stops

15:00 - 09:00ORD-SYD

25h 00m1 stop

$1,481American Airlines

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Tue, 30 Sep - Wed, 12 Nov

09:10 - 21:22SYD-ORD

27h 12m1 stop

12:15 - 06:10ORD-SYD

24h 55m1 stop

$1,580American Airlines

Find Deal

Sat, 4 Oct - Tue, 23 Dec

09:30 - 17:05SYD-ORD

22h 35m2 stops

14:17 - 07:00ORD-SYD

23h 43m1 stop

$1,582United Airlines

Find Deal

Sat, 4 Oct - Tue, 23 Dec

12:25 - 05:16SYD-ORD

33h 51m2 stops

16:25 - 20:15ORD-SYD

34h 50m1 stop

$1,711ANA

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Thu, 19 Feb - Thu, 26 Feb

11:20 - 14:25SYD-ORD

20h 05m1 stop

16:16 - 09:15ORD-SYD

23h 59m1 stop

$1,756United Airlines

Find Deal

Mon, 8 Dec - Wed, 21 Jan

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

8 Nov

SYD11:20Sydney Kingsford Smith

44h 50m

2 stops

ORD15:10Chicago O'Hare Intl

22 Nov

ORD15:40Chicago O'Hare Intl

24h 55m

1 stop

SYD09:35Sydney Kingsford Smith

$1,303

Find similar

Air Canada

8 Nov

SYD11:20Sydney Kingsford Smith

25h 10m

2 stops

ORD19:30Chicago O'Hare Intl

22 Nov

ORD08:00Chicago O'Hare Intl

32h 35m

2 stops

SYD09:35Sydney Kingsford Smith

$1,316

Find similar

Air Canada

29 Oct

SYD10:20Sydney Kingsford Smith

37h 40m

2 stops

ORD08:00Chicago O'Hare Intl

5 Nov

ORD15:40Chicago O'Hare Intl

24h 55m

1 stop

SYD09:35Sydney Kingsford Smith

$1,322

Find similar

United Airlines flights from Sydney to Chicago

Our best United Airlines deals on Sydney to Chicago flight tickets

United Airlines

4 Oct

SYD09:30Sydney Kingsford Smith

22h 35m

2 stops

ORD17:05Chicago O'Hare Intl

23 Dec

ORD14:17Chicago O'Hare Intl

23h 43m

1 stop

SYD07:00Sydney Kingsford Smith

$1,582

Find similar

United Airlines

8 Dec

SYD11:20Sydney Kingsford Smith

20h 05m

1 stop

ORD14:25Chicago O'Hare Intl

21 Jan

ORD16:16Chicago O'Hare Intl

23h 59m

1 stop

SYD09:15Sydney Kingsford Smith

$1,756

Find similar

United Airlines

12 Jan

SYD14:00Sydney Kingsford Smith

26h 14m

1 stop

ORD23:14Chicago O'Hare Intl

30 Jan

ORD16:10Chicago O'Hare Intl

23h 55m

1 stop

SYD09:05Sydney Kingsford Smith

$1,765

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

11:20-15:10

2 stops44h 50m

Chicago O'Hare Intl

Sat 22/11

15:40-09:35

1 stop24h 55m

$1,303

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

11:20-19:30

2 stops25h 10m

Chicago O'Hare Intl

Sat 22/11

08:00-09:35

2 stops32h 35m

$1,316

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 29/10

10:20-08:00

2 stops37h 40m

Chicago O'Hare Intl

Wed 5/11

15:40-09:35

1 stop24h 55m

$1,322

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 30/10

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 6/11

15:40-09:35

1 stop24h 55m

$1,325

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:10-15:51

1 stop21h 41m

Chicago O'Hare Intl

Wed 12/11

18:03-09:00

1 stop21h 57m

$1,421

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:10-17:18

2 stops23h 08m

Chicago O'Hare Intl

Wed 12/11

15:00-09:00

1 stop25h 00m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 4/10

09:10-21:22

1 stop27h 12m

Chicago O'Hare Intl

Tue 23/12

12:15-06:10

1 stop24h 55m

$1,580

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 4/10

09:30-17:05

2 stops22h 35m

Chicago O'Hare Intl

Tue 23/12

14:17-07:00

1 stop23h 43m

$1,582

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

12:25-05:16

2 stops33h 51m

Chicago O'Hare Intl

Thu 26/2

16:25-20:15

1 stop34h 50m

$1,711

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 8/12

11:20-14:25

1 stop20h 05m

Chicago O'Hare Intl

Wed 21/1

16:16-09:15

1 stop23h 59m

$1,756

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 $1,117.

What is the cheapest day to depart on your flight to Chicago?

Our data shows that Tuesday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $1,685. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $1,984. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Sydney to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as $1,682. Flights in the morning are often more expensive, with an average ticket price of $1,861.

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 $1,477 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 $1,165 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 34% 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 2025, prices for Sydney to Chicago flights are approximately 55% 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

Direct flights	None

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

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How far is Sydney Kingsford Smith to Chicago by plane?
There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 05m 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 September 2025.
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 (57% of total bookings). The next most popular airlines are Air Canada (17%), United Airlines (11%), and ANA (5%).

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 $988	Free cancellation	Rating 7.5 905 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,170	Free cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,173	Free cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,529	Free cancellation	Rating 8.0 505 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,577	Free cancellation	Rating 8.4 961 reviews	Search ANA flights
United Airlines	PriceFrom $1,628	Free cancellation	Rating 7.4 8,929 reviews	Search United Airlines 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 $638

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 15/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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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Cheap last-minute flights

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

United Airlines flights from Sydney to Chicago

Our best United Airlines deals on Sydney to Chicago flight tickets

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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

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 $1,117.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Sydney to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as $1,682. Flights in the morning are often more expensive, with an average ticket price of $1,861.

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 34% 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 2025, prices for Sydney to Chicago flights are approximately 55% 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 Canada, Etihad Airways, and Cathay Pacific 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: 65% 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 Los Angeles (LAX) offer the lowest average return price of $1,186.

Which stopover airport has the shortest travel time from Sydney to Chicago?

Flights connecting via Vancouver (YVR) have the shortest average one-way travel time: 20h 18m.

Which stopover airport has the shortest connection time from Sydney to Chicago?

Dallas (DFW) has the shortest average stopover time for this route: 2h 10m.

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

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