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.

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 stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Vancouver (YVR) offer the lowest average return price of $1,212.

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

Los Angeles (LAX) was the most common stop: 68% 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 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 64% 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 December 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.

$905 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 typical for flights on this route. Typical prices usually range from $1,119 to $2,796. The lowest price recently found on this route was $1,515.

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11:20 - 22:05

SYD

ORD

27h 45m2 stops

15:35 - 09:35

ORD

SYD

25h 00m1 stop

$1,515Air Canada

Tue, 27 Jan - Tue, 24 Feb

11:20 - 22:05

SYD

ORD

27h 45m2 stops

11:11 - 09:35

ORD

SYD

29h 24m2 stops

$1,525Air Canada

Tue, 27 Jan - Tue, 24 Feb

11:20 - 16:42

SYD

ORD

22h 22m1 stop

13:05 - 09:35

ORD

SYD

27h 30m1 stop

$1,536Air Canada

Tue, 27 Jan - Tue, 24 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

07:15 - 09:35

ORD

SYD

33h 20m2 stops

$1,557Air Canada

Wed, 11 Feb - Wed, 18 Feb

11:20 - 20:10

SYD

ORD

49h 50m2 stops

07:15 - 09:35

ORD

SYD

33h 20m2 stops

$1,563Air Canada

Wed, 11 Feb - Wed, 18 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

07:15 - 09:35

ORD

SYD

33h 20m2 stops

$1,572Air Canada

Tue, 10 Feb - Tue, 17 Feb

11:20 - 20:10

SYD

ORD

25h 50m2 stops

10:00 - 09:35

ORD

SYD

30h 35m2 stops

$1,573Air Canada

Tue, 10 Feb - Tue, 17 Feb

11:20 - 14:41

SYD

ORD

20h 21m1 stop

15:35 - 09:35

ORD

SYD

25h 00m1 stop

$1,591Air Canada

Wed, 11 Feb - Wed, 18 Feb

09:15 - 18:45

SYD

MDW

24h 30m2 stops

14:12 - 06:35

MDW

SYD

25h 23m2 stops

$2,069Delta

Mon, 20 Apr - Wed, 6 May

09:15 - 17:54

SYD

MDW

23h 39m2 stops

13:10 - 06:35

MDW

SYD

26h 25m2 stops

$2,143Delta

Sun, 19 Apr - Tue, 5 May

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

27 Jan

SYD11:20Sydney Kingsford Smith

27h 45m

2 stops

ORD22:05Chicago O'Hare Intl

24 Feb

ORD15:35Chicago O'Hare Intl

25h 00m

1 stop

SYD09:35Sydney Kingsford Smith

$1,515

Find similar

Air Canada

27 Jan

SYD11:20Sydney Kingsford Smith

27h 45m

2 stops

ORD22:05Chicago O'Hare Intl

24 Feb

ORD11:11Chicago O'Hare Intl

29h 24m

2 stops

SYD09:35Sydney Kingsford Smith

$1,525

Find similar

Air Canada

27 Jan

SYD11:20Sydney Kingsford Smith

22h 22m

1 stop

ORD16:42Chicago O'Hare Intl

24 Feb

ORD13:05Chicago O'Hare Intl

27h 30m

1 stop

SYD09:35Sydney Kingsford Smith

$1,536

Find similar

United Airlines flights from Sydney to Chicago

Our best United Airlines deals on Sydney to Chicago flight tickets

United Airlines

16 Jan

SYD11:20Sydney Kingsford Smith

20h 30m

1 stop

ORD14:50Chicago O'Hare Intl

31 Jan

ORD19:58Chicago O'Hare Intl

41h 22m

1 stop

SYD06:20Sydney Kingsford Smith

$1,801

Find similar

United Airlines

30 Dec

SYD12:10Sydney Kingsford Smith

23h 35m

2 stops

ORD18:45Chicago O'Hare Intl

5 Mar

ORD16:08Chicago O'Hare Intl

23h 57m

2 stops

SYD09:05Sydney Kingsford Smith

$1,804

Find similar

United Airlines

16 Jan

SYD14:00Sydney Kingsford Smith

22h 51m

2 stops

ORD19:51Chicago O'Hare Intl

31 Jan

ORD16:16Chicago O'Hare Intl

21h 04m

1 stop

SYD06:20Sydney Kingsford Smith

$1,877

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 27/1

11:20-22:05

2 stops27h 45m

Chicago O'Hare Intl

Tue 24/2

15:35-09:35

1 stop25h 00m

$1,515

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 27/1

11:20-22:05

2 stops27h 45m

Chicago O'Hare Intl

Tue 24/2

11:11-09:35

2 stops29h 24m

$1,525

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 27/1

11:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Tue 24/2

13:05-09:35

1 stop27h 30m

$1,536

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 18/2

07:15-09:35

2 stops33h 20m

$1,557

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/2

11:20-20:10

2 stops49h 50m

Chicago O'Hare Intl

Wed 18/2

07:15-09:35

2 stops33h 20m

$1,563

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 17/2

07:15-09:35

2 stops33h 20m

$1,572

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/2

11:20-20:10

2 stops25h 50m

Chicago O'Hare Intl

Tue 17/2

10:00-09:35

2 stops30h 35m

$1,573

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 18/2

15:35-09:35

1 stop25h 00m

$1,591

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 20/4

09:15-18:45

2 stops24h 30m

Chicago Midway

Wed 6/5

14:12-06:35

2 stops25h 23m

$2,069

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 19/4

09:15-17:54

2 stops23h 39m

Chicago Midway

Tue 5/5

13:10-06:35

2 stops26h 25m

$2,143

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 $1,097.

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 $1,430 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 $1,149 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 63% 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 December 2025, prices for Sydney to Chicago flights are approximately 61% 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 43m
Direct flights	None

The fastest flight from Sydney to Chicago takes 19h 43m

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 43m 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 December 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 (60% of total bookings). The next most popular airlines are Air Canada (15%), 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 $976	Free cancellation	Rating 7.5 957 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,161	Free cancellation	Rating 7.2 11,074 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,163	Free cancellation	Rating 7.1 10,564 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,408	Free cancellation	Rating 8.0 562 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,472	Free cancellation	Rating 7.4 9,121 reviews	Search United Airlines flights
ANA	PriceFrom $1,563	Free cancellation	Rating 8.4 1,051 reviews	Search ANA flights
Virgin Australia	PriceFrom $1,715	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.

Start using Trips

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Cheap flights from Sydney to Chicago from $905

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 15/1. 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

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Find the cheapest flights from Sydney to Chicago

Cheap return flights

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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

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 May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,097.

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 63% 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 December 2025, prices for Sydney to Chicago flights are approximately 61% 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: 68% 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 $1,212.

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