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 17m.

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 66% 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.

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

United Airlines 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?

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.

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

Flights via Los Angeles (LAX) offer the lowest average return price of $1,203.

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 August 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.

$691 Cheap Flights from Sydney to Chicago (SYD-CHI) in 2025

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 $1,331 to $1,847. The lowest price recently found on this route was $1,540.

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Find the cheapest flights from Sydney to Chicago (SYD-CHI)

Round-trip

One-way

Cheap return flights

09:30 - 18:14SYD-ORD

23h 44m1 stop

12:54 - 07:00ORD-SYD

27h 06m1 stop

$1,540

Find Deal

Thu, 4 Sep - Fri, 19 Sep

21:45 - 07:20SYD-ORD

26h 35m1 stop

18:05 - 20:15ORD-SYD

33h 10m2 stops

$1,622ANA

Find Deal

Wed, 3 Dec - Mon, 8 Dec

09:55 - 06:10SYD-ORD

36h 15m2 stops

16:25 - 12:40ORD-SYD

28h 15m2 stops

$1,671Air New Zealand

Find Deal

Fri, 10 Oct - Fri, 24 Oct

09:10 - 15:55SYD-ORD

45h 45m1 stop

19:01 - 07:05ORD-SYD

21h 04m1 stop

$1,737American Airlines

Find Deal

Sat, 30 Aug - Sat, 6 Sep

09:10 - 17:18SYD-ORD

23h 08m2 stops

19:01 - 07:05ORD-SYD

21h 04m1 stop

$1,743American Airlines

Find Deal

Fri, 5 Sep - Thu, 18 Sep

11:50 - 22:41SYD-ORD

25h 51m2 stops

16:10 - 08:45ORD-SYD

25h 35m2 stops

$1,758Air New Zealand

Find Deal

Wed, 27 Aug - Sat, 30 Aug

11:50 - 14:53SYD-ORD

20h 03m1 stop

10:40 - 06:20ORD-SYD

26h 40m2 stops

$1,760United Airlines

Find Deal

Sat, 15 Nov - Thu, 15 Jan

12:10 - 00:15SYD-ORD

29h 05m2 stops

14:10 - 09:15ORD-SYD

26h 05m2 stops

$1,763United Airlines

Find Deal

Mon, 15 Dec - Thu, 15 Jan

11:20 - 08:00SYD-ORD

37h 40m2 stops

07:15 - 09:35ORD-SYD

33h 20m2 stops

$1,864Air Canada

Find Deal

Wed, 3 Dec - Mon, 8 Dec

11:20 - 17:10SYD-ORD

46h 50m2 stops

07:15 - 09:35ORD-SYD

33h 20m3 stops

$1,875Air Canada

Find Deal

Wed, 3 Dec - Mon, 8 Dec

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets

ANA

3 Dec

SYD21:45Sydney Kingsford Smith

26h 35m

1 stop

ORD07:20Chicago O'Hare Intl

8 Dec

ORD18:05Chicago O'Hare Intl

33h 10m

2 stops

SYD20:15Sydney Kingsford Smith

$1,622

Find similar

ANA

25 Aug

SYD11:50Sydney Kingsford Smith

32h 11m

2 stops

ORD05:01Chicago O'Hare Intl

1 Sept

ORD17:45Chicago O'Hare Intl

34h 30m

1 stop

SYD19:15Sydney Kingsford Smith

$1,634

Find similar

ANA

4 Sept

SYD11:50Sydney Kingsford Smith

32h 11m

2 stops

ORD05:01Chicago O'Hare Intl

19 Sept

ORD17:45Chicago O'Hare Intl

34h 30m

1 stop

SYD19:15Sydney Kingsford Smith

$1,735

Find similar

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets

Air Canada

3 Dec

SYD11:20Sydney Kingsford Smith

37h 40m

2 stops

ORD08:00Chicago O'Hare Intl

8 Dec

ORD07:15Chicago O'Hare Intl

33h 20m

2 stops

SYD09:35Sydney Kingsford Smith

$1,864

Find similar

Air Canada

3 Dec

SYD11:20Sydney Kingsford Smith

46h 50m

2 stops

ORD17:10Chicago O'Hare Intl

8 Dec

ORD07:15Chicago O'Hare Intl

33h 20m

3 stops

SYD09:35Sydney Kingsford Smith

$1,875

Find similar

Air Canada

28 Oct

SYD10:20Sydney Kingsford Smith

20h 21m

1 stop

ORD14:41Chicago O'Hare Intl

30 Oct

ORD15:40Chicago O'Hare Intl

24h 55m

1 stop

SYD08:35Sydney Kingsford Smith

$2,024

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 4/9

09:30-18:14

1 stop23h 44m

Chicago O'Hare Intl

Fri 19/9

12:54-07:00

1 stop27h 06m

$1,540

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 3/12

21:45-07:20

1 stop26h 35m

Chicago O'Hare Intl

Mon 8/12

18:05-20:15

2 stops33h 10m

$1,622

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 10/10

09:55-06:10

2 stops36h 15m

Chicago O'Hare Intl

Fri 24/10

16:25-12:40

2 stops28h 15m

$1,671

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 30/8

09:10-15:55

1 stop45h 45m

Chicago O'Hare Intl

Sat 6/9

19:01-07:05

1 stop21h 04m

$1,737

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 5/9

09:10-17:18

2 stops23h 08m

Chicago O'Hare Intl

Thu 18/9

19:01-07:05

1 stop21h 04m

$1,743

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 27/8

11:50-22:41

2 stops25h 51m

Chicago O'Hare Intl

Sat 30/8

16:10-08:45

2 stops25h 35m

$1,758

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 15/11

11:50-14:53

1 stop20h 03m

Chicago O'Hare Intl

Thu 15/1

10:40-06:20

2 stops26h 40m

$1,760

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 15/12

12:10-00:15

2 stops29h 05m

Chicago O'Hare Intl

Thu 15/1

14:10-09:15

2 stops26h 05m

$1,763

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 3/12

11:20-08:00

2 stops37h 40m

Chicago O'Hare Intl

Mon 8/12

07:15-09:35

2 stops33h 20m

$1,864

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 3/12

11:20-17:10

2 stops46h 50m

Chicago O'Hare Intl

Mon 8/12

07:15-09:35

3 stops33h 20m

$1,875

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 February, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,144.

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 $1,724. Flights from Sydney to Chicago on a Saturday will generally be more expensive and average around $2,030. 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 $1,721. Flights in the morning are often more expensive, with an average ticket price of $1,904.

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 $1,569 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 $1,192 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 August 2025, prices for Sydney to Chicago flights are approximately 57% 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

Best price found	$691
Fastest flight time	19h 40m
Direct flights	None
Airports in Chicago	2 airports

The best one-way flight to Chicago from Sydney in the past 72 hours is $691. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,540.

The fastest flight from Sydney to Chicago takes 19h 40m

There are no direct flights from Sydney to Chicago. Popular non-direct routes for this connection are Sydney Kingsford Smith Airport - Chicago Midway Airport and Sydney Kingsford Smith Airport - Chicago O'Hare Intl Airport.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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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 40m 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 August 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 (56% of total bookings). The next most popular airlines are Air Canada (18%), United Airlines (10%), and ANA (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 $1,013	Free cancellation	Rating 7.5 895 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,198	Free cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Air Canada	PriceFrom $1,269	Free cancellation	Rating 7.1 9,977 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,565	Free cancellation	Rating 8.0 504 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,613	Free cancellation	Rating 8.4 933 reviews	Search ANA flights
United Airlines	PriceFrom $1,666	Free cancellation	Rating 7.4 8,919 reviews	Search United Airlines flights
Virgin Australia	PriceFrom $1,770	Free cancellation	Rating 7.5 411 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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Find better results for your trip to the United States

Cheap flights from Sydney to Chicago from $691

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

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Sydney to Chicago (SYD-CHI)

Cheap return flights

Cheap one-way flights

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets

Air Canada flights from Sydney to Chicago

Our best Air Canada 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

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 February, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,144.

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 $1,721. Flights in the morning are often more expensive, with an average ticket price of $1,904.

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 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 August 2025, prices for Sydney to Chicago flights are approximately 57% cheaper when compared to flights at the same time last year.

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

United Airlines and Etihad Airways 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 $1,203.

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 17m.

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

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