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: 20h 04m.

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

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

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

Los Angeles (LAX) was the most common stop: 63% 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 $1,215.

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 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 connection time from Sydney to Chicago?

Houston (IAH) has the shortest average stopover time for this route: 1h 43m.

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 November 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.

$813 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 $1,754 to $2,442. The lowest price recently found on this route was $1,610.

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08:45 - 23:11SYD-ORD

29h 26m2 stops

17:15 - 17:10ORD-SYD

32h 55m2 stops

$1,610Air New Zealand

Find Deal

Wed, 15 Apr - Wed, 29 Apr

11:50 - 05:01SYD-ORD

32h 11m2 stops

17:45 - 19:15ORD-SYD

34h 30m1 stop

$1,777ANA

Find Deal

Wed, 15 Apr - Wed, 29 Apr

11:20 - 20:10SYD-ORD

25h 50m2 stops

12:50 - 09:35ORD-SYD

27h 45m2 stops

$1,830Air Canada

Find Deal

Mon, 2 Feb - Thu, 19 Feb

11:20 - 20:10SYD-ORD

25h 50m2 stops

07:15 - 09:35ORD-SYD

33h 20m3 stops

$1,841Air Canada

Find Deal

Mon, 2 Feb - Thu, 19 Feb

11:50 - 21:11SYD-ORD

24h 21m2 stops

16:40 - 08:45ORD-SYD

25h 05m2 stops

$1,849Air New Zealand

Find Deal

Sat, 16 May - Sat, 6 Jun

11:20 - 08:05SYD-ORD

37h 45m2 stops

13:05 - 09:35ORD-SYD

27h 30m1 stop

$1,876Air Canada

Find Deal

Mon, 2 Feb - Thu, 19 Feb

11:20 - 16:38SYD-ORD

22h 18m1 stop

10:35 - 09:35ORD-SYD

30h 00m2 stops

$1,878Air Canada

Find Deal

Thu, 12 Feb - Thu, 26 Feb

11:20 - 17:08SYD-ORD

22h 48m2 stops

08:45 - 09:35ORD-SYD

31h 50m2 stops

$1,880Air Canada

Find Deal

Tue, 3 Feb - Sat, 7 Feb

09:25 - 18:31SYD-MDW

24h 06m2 stops

14:00 - 06:35MDW-SYD

25h 35m2 stops

$2,090Delta

Find Deal

Mon, 11 May - Mon, 1 Jun

10:40 - 17:34SYD-MDW

23h 54m2 stops

13:26 - 06:50MDW-SYD

24h 24m2 stops

$2,157Delta

Find Deal

Thu, 15 Jan - Sat, 31 Jan

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

2 Feb

SYD11:20Sydney Kingsford Smith

25h 50m

2 stops

ORD20:10Chicago O'Hare Intl

19 Feb

ORD12:50Chicago O'Hare Intl

27h 45m

2 stops

SYD09:35Sydney Kingsford Smith

$1,830

Find similar

Air Canada

2 Feb

SYD11:20Sydney Kingsford Smith

25h 50m

2 stops

ORD20:10Chicago O'Hare Intl

19 Feb

ORD07:15Chicago O'Hare Intl

33h 20m

3 stops

SYD09:35Sydney Kingsford Smith

$1,841

Find similar

Air Canada

2 Feb

SYD11:20Sydney Kingsford Smith

37h 45m

2 stops

ORD08:05Chicago O'Hare Intl

19 Feb

ORD13:05Chicago O'Hare Intl

27h 30m

1 stop

SYD09:35Sydney Kingsford Smith

$1,876

Find similar

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

16 May

SYD11:50Sydney Kingsford Smith

24h 21m

2 stops

ORD21:11Chicago O'Hare Intl

6 June

ORD16:40Chicago O'Hare Intl

25h 05m

2 stops

SYD08:45Sydney Kingsford Smith

$1,849

Find similar

Air New Zealand

16 May

SYD11:50Sydney Kingsford Smith

25h 52m

2 stops

ORD22:42Chicago O'Hare Intl

6 June

ORD16:40Chicago O'Hare Intl

25h 05m

2 stops

SYD08:45Sydney Kingsford Smith

$2,002

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 15/4

08:45-23:11

2 stops29h 26m

Chicago O'Hare Intl

Wed 29/4

17:15-17:10

2 stops32h 55m

$1,610

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 15/4

11:50-05:01

2 stops32h 11m

Chicago O'Hare Intl

Wed 29/4

17:45-19:15

1 stop34h 30m

$1,777

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-20:10

2 stops25h 50m

Chicago O'Hare Intl

Thu 19/2

12:50-09:35

2 stops27h 45m

$1,830

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-20:10

2 stops25h 50m

Chicago O'Hare Intl

Thu 19/2

07:15-09:35

3 stops33h 20m

$1,841

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 16/5

11:50-21:11

2 stops24h 21m

Chicago O'Hare Intl

Sat 6/6

16:40-08:45

2 stops25h 05m

$1,849

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-08:05

2 stops37h 45m

Chicago O'Hare Intl

Thu 19/2

13:05-09:35

1 stop27h 30m

$1,876

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 12/2

11:20-16:38

1 stop22h 18m

Chicago O'Hare Intl

Thu 26/2

10:35-09:35

2 stops30h 00m

$1,878

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/2

11:20-17:08

2 stops22h 48m

Chicago O'Hare Intl

Sat 7/2

08:45-09:35

2 stops31h 50m

$1,880

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 11/5

09:25-18:31

2 stops24h 06m

Chicago Midway

Mon 1/6

14:00-06:35

2 stops25h 35m

$2,090

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 15/1

10:40-17:34

2 stops23h 54m

Chicago Midway

Sat 31/1

13:26-06:50

2 stops24h 24m

$2,157

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 May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,148.

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 $1,741. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $2,050. 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 $1,738. Flights in the morning are often more expensive, with an average ticket price of $1,923.

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 $1,513 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 $1,203 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 56% 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 November 2025, prices for Sydney to Chicago flights are approximately 44% 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. 19h 45m 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 November 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 (59% of total bookings). The next most popular airlines are Air Canada (16%), United Airlines (10%), 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 $1,020	Free cancellation	Rating 7.5 942 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,209	Free cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,212	Free cancellation	Rating 7.1 10,464 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,544	Free cancellation	Rating 8.0 533 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,629	Free cancellation	Rating 8.4 1,010 reviews	Search ANA flights
United Airlines	PriceFrom $1,682	Free cancellation	Rating 7.4 9,034 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 $813

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 5/3. 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

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Sydney to Chicago

Cheap return flights

Cheap one-way flights

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand 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.

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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 May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,148.

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 $1,738. Flights in the morning are often more expensive, with an average ticket price of $1,923.

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 56% 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 November 2025, prices for Sydney to Chicago flights are approximately 44% cheaper when compared to flights at the same time last year.

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

Delta is the most popular carrier 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: 63% 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 $1,215.

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: 20h 04m.

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

Houston (IAH) has the shortest average stopover time for this route: 1h 43m.

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