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

Flights via Houston (IAH) offer the lowest average return price of $1,508.

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

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

Los Angeles (LAX) was the most common stop: 41% of momondo users choosing one-stop flights on this route connected there.

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 44% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 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 San Francisco (SFO) have the shortest average one-way travel time: 19h 30m.

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 5 as of September 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.

$550 Cheap Flights from Sydney to Chicago in 2026

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Find the cheapest flights from Sydney to Chicago

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One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

14:15 - 05:16SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

31h 01m3 stops Nadi Los Angeles Las Vegas Harry Reid Intl

06:30 - 12:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

38h 05m3 stops Denver Intl Los Angeles Nadi

$1,404Multiple Airlines

Mon, 19 Oct - Mon, 26 Oct

21:25 - 05:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 34m1 stop San Francisco

21:00 - 06:25ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

40h 25m1 stop Los Angeles

$1,460Qantas Airways

Fri, 4 Dec - Sat, 5 Dec

18:50 - 06:34SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

27h 44m1 stop Los Angeles

20:01 - 07:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

43h 29m1 stop Los Angeles

$1,632Multiple Airlines

Fri, 9 Oct - Sat, 17 Oct

11:50 - 21:45SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

26h 55m2 stops Auckland Intl San Francisco

09:15 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

30h 20m2 stops Houston George Bush Intcntl Auckland Intl

$1,751Air New Zealand

Wed, 4 Nov - Mon, 9 Nov

07:30 - 20:35SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 05m2 stops Auckland Intl Los Angeles

14:00 - 10:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

27h 35m2 stops Los Angeles Auckland Intl

$1,772Air New Zealand

Tue, 3 Nov - Wed, 11 Nov

20:30 - 10:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 35m2 stops Honolulu Dallas/Fort Worth

06:29 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 31m1 stop Los Angeles

$1,831American Airlines

Wed, 4 Nov - Mon, 9 Nov

20:30 - 10:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 35m2 stops Honolulu Dallas/Fort Worth

06:29 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 31m1 stop Los Angeles

$1,833American Airlines

Wed, 4 Nov - Mon, 9 Nov

13:00 - 18:35SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 35m1 stop Dallas/Fort Worth

08:29 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

32h 31m1 stop Los Angeles

$1,896Qantas Airways

Mon, 12 Oct - Mon, 26 Oct

11:20 - 08:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

37h 40m3 stops Vancouver Intl Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

13:55 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$2,252Air Canada

Wed, 4 Nov - Mon, 9 Nov

11:20 - 08:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

37h 40m3 stops Vancouver Intl Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

13:55 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$2,291Air Canada

Tue, 3 Nov - Wed, 11 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

17:50 - 06:17SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

27h 27m1 stop Los Angeles

06:30 - 06:25ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

30h 55m2 stops Denver Intl Los Angeles

$1,825Multiple Airlines

Tue, 8 Sep - Thu, 5 Nov

07:50 - 00:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

32h 09m2 stops Auckland Intl Houston George Bush Intcntl

15:00 - 08:45ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 45m2 stops Los Angeles Auckland Intl

$1,915Air New Zealand

Thu, 10 Sep - Sun, 13 Sep

14:05 - 14:20SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

39h 15m1 stop Hong Kong Intl

14:10 - 12:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 50m1 stop Hong Kong Intl

$2,105Cathay Pacific

Tue, 8 Sep - Thu, 5 Nov

20:45 - 12:07SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 22m2 stops Honolulu Seattle/Tacoma Intl

18:35 - 19:45ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

32h 10m2 stops Seattle/Tacoma Intl Honolulu

$2,175Multiple Airlines

Tue, 8 Sep - Thu, 5 Nov

20:45 - 13:22SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

31h 37m2 stops Honolulu San Diego

18:35 - 19:45ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

32h 10m2 stops Seattle/Tacoma Intl Honolulu

$2,216Multiple Airlines

Tue, 8 Sep - Thu, 5 Nov

09:20 - 11:51SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

41h 31m3 stops Vancouver Intl Los Angeles Atlanta Hartsfield-Jackson

06:30 - 07:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 50m3 stops Denver Intl Los Angeles Vancouver Intl

$2,227Multiple Airlines

Fri, 11 Sep - Sun, 13 Sep

09:20 - 00:28SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 08m3 stops Vancouver Intl Toronto Pearson Intl Newark

07:09 - 07:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 11m2 stops Toronto Pearson Intl Vancouver Intl

$3,105Air Canada

Fri, 11 Sep - Sun, 13 Sep

06:30 - 14:43SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

23h 13m2 stops Brisbane Vancouver Intl

11:05 - 07:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 15m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$6,396Air Canada

Thu, 10 Sep - Sun, 13 Sep

06:30 - 14:43SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

23h 13m2 stops Brisbane Vancouver Intl

11:05 - 07:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 15m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$6,399Air Canada

Thu, 10 Sep - Sun, 13 Sep

07:00 - 14:43SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 43m2 stops Brisbane Vancouver Intl

11:05 - 07:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

29h 15m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$6,476Air Canada

Fri, 11 Sep - Sun, 13 Sep

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Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

4 Dec

SYD21:25Sydney Kingsford Smith

25h 34m

1 stop

ORD05:59Chicago O'Hare Intl

5 Dec

ORD21:00Chicago O'Hare Intl

40h 25m

1 stop

SYD06:25Sydney Kingsford Smith

$1,460

Qantas Airways

12 Oct

SYD13:00Sydney Kingsford Smith

21h 35m

1 stop

ORD18:35Chicago O'Hare Intl

26 Oct

ORD08:29Chicago O'Hare Intl

32h 31m

1 stop

SYD09:00Sydney Kingsford Smith

$1,896

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Cathay Pacific

3 Nov

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD12:30Chicago O'Hare Intl

11 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,756

Cathay Pacific

4 Nov

SYD22:20Sydney Kingsford Smith

31h 35m

1 stop

ORD12:55Chicago O'Hare Intl

9 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,763

Cathay Pacific

29 Oct

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD13:30Chicago O'Hare Intl

11 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,765

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 19/10

14:15-05:16

3 stops31h 01m

Chicago O'Hare Intl

Mon 26/10

06:30-12:35

3 stops38h 05m

$1,404

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 4/12

21:25-05:59

1 stop25h 34m

Chicago O'Hare Intl

Sat 5/12

21:00-06:25

1 stop40h 25m

$1,460

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 9/10

18:50-06:34

1 stop27h 44m

Chicago O'Hare Intl

Sat 17/10

20:01-07:30

1 stop43h 29m

$1,632

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

11:50-21:45

2 stops26h 55m

Chicago O'Hare Intl

Mon 9/11

09:15-08:35

2 stops30h 20m

$1,751

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 3/11

07:30-20:35

2 stops30h 05m

Chicago O'Hare Intl

Wed 11/11

14:00-10:35

2 stops27h 35m

$1,772

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

20:30-10:05

2 stops30h 35m

Chicago O'Hare Intl

Mon 9/11

06:29-09:00

1 stop33h 31m

$1,831

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

20:30-10:05

2 stops30h 35m

Chicago O'Hare Intl

Mon 9/11

06:29-09:00

1 stop33h 31m

$1,833

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 12/10

13:00-18:35

1 stop21h 35m

Chicago O'Hare Intl

Mon 26/10

08:29-09:00

1 stop32h 31m

$1,896

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

11:20-08:00

3 stops37h 40m

Chicago O'Hare Intl

Mon 9/11

13:55-09:35

2 stops26h 40m

$2,252

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 3/11

11:20-08:00

3 stops37h 40m

Chicago O'Hare Intl

Wed 11/11

13:55-09:35

2 stops26h 40m

$2,291

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $1,225 to $2,129.
The lowest price recently found on this route was $1,404.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in October, then you should wait until September to fly from Sydney, when ticket prices are also cheap, with an average price of $1,478.

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 $1,945 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 $1,214 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 17% 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 2026, prices for Sydney to Chicago flights are approximately 1% more expensive 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	$550
Fastest flight time	23h 45m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $550. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,404.

The fastest flight from Sydney to Chicago takes 23h 45m

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

Search flight deals

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. 23h 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 5 as of September 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 (30% of total bookings). The next most popular airlines are Air Canada (24%), United Airlines (23%), and American Airlines (12%).

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 $1,051	Free cancellation	Rating 7.1 11,592 reviews	Search Air Canada flights
American Airlines	PriceFrom $1,226	Free cancellation	Rating 7.1 12,041 reviews	Search American Airlines flights
Qantas Airways	PriceFrom $1,229	Free cancellation	Rating 7.5 1,090 reviews	Search Qantas Airways flights
Air New Zealand	PriceFrom $1,313	Free cancellation	Rating 8.0 668 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,372	Free cancellation	Rating 7.4 10,173 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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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Sydney to Chicago from $550

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 20/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific 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?

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

Best price found

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

Fly to other destinations from Sydney

According to popular flight searches on momondo this year

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