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 stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Vancouver (YVR) offer the lowest average return price of $1,388.

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

Etihad Airways and Philippine Airlines are the most popular carriers 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: 47% of momondo users choosing one-stop flights on this route connected there.

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.

Which airlines fly to Chicago?

Qantas Airways, Air New Zealand and Air Canada 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 46% 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.

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 October 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.

$632 Cheap Flights from Sydney to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Sydney to Chicago

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One-way

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Enter your travel dates to find the best prices.

11:10 - 16:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 50m2 stops Los Angeles Denver Intl

13:44 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 16m2 stops Dallas/Fort Worth Los Angeles

$1,060American Airlines

Tue, 10 Nov - Wed, 25 Nov

11:10 - 16:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 55m1 stop Los Angeles

22:03 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

41h 57m1 stop Los Angeles

$1,060American Airlines

Tue, 10 Nov - Sat, 21 Nov

11:10 - 16:05SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 55m1 stop Los Angeles

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

31h 31m1 stop Los Angeles

$1,150Qantas Airways

Fri, 6 Nov - Mon, 23 Nov

11:10 - 22:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

28h 20m1 stop Los Angeles

15:21 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 39m2 stops Denver Intl Los Angeles

$1,211Qantas Airways

Fri, 6 Nov - Mon, 23 Nov

14:00 - 05:13SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

32h 13m3 stops Nadi Los Angeles Las Vegas Harry Reid Intl

11:35 - 12:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

32h 00m3 stops Phoenix Sky Harbor Intl Los Angeles Nadi

$1,412Multiple Airlines

Mon, 2 Nov - Mon, 23 Nov

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

$1,578Multiple Airlines

Fri, 16 Oct - Sat, 31 Oct

14:05 - 00:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

27h 54m2 stops Auckland Intl Los Angeles

15:00 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 35m2 stops Los Angeles Auckland Intl

$1,745Air New Zealand

Fri, 6 Nov - Mon, 23 Nov

09:55 - 22:29SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

29h 34m2 stops Auckland Intl San Francisco

12:42 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 53m2 stops San Francisco Auckland Intl

$1,759Air New Zealand

Wed, 4 Nov - Thu, 12 Nov

10:20 - 19:52SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 32m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

07:05 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 30m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$2,642Air Canada

Tue, 27 Oct - Thu, 26 Nov

10:20 - 19:52SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 32m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

07:05 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 30m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$2,685Air Canada

Mon, 26 Oct - Sat, 31 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

10:10 - 18:38SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

24h 28m1 stop Los Angeles

12:00 - 08:05ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 05m1 stop Los Angeles

$1,080American Airlines

Mon, 5 Oct - Mon, 19 Oct

10:10 - 15:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 49m1 stop Los Angeles

11:45 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 15m1 stop Los Angeles

$1,150American Airlines

Wed, 7 Oct - Thu, 12 Nov

10:10 - 15:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

21h 49m1 stop Los Angeles

17:59 - 11:45ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 46m2 stops Dallas/Fort Worth Brisbane

$1,216Qantas Airways

Wed, 7 Oct - Thu, 12 Nov

20:50 - 15:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

35h 05m1 stop Abu Dhabi Zayed Intl

20:25 - 06:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 10m1 stop Abu Dhabi Zayed Intl

$1,923Etihad Airways

Mon, 5 Oct - Tue, 13 Oct

10:10 - 18:38SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

24h 28m1 stop Los Angeles

18:45 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 15m1 stop Los Angeles

$1,943Qantas Airways

Wed, 7 Oct - Thu, 12 Nov

10:10 - 00:30SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 20m1 stop Los Angeles

17:53 - 08:05ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

22h 12m1 stop Los Angeles

$1,986American Airlines

Mon, 5 Oct - Sun, 18 Oct

22:05 - 09:40SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

51h 35m2 stops Kuala Lumpur Intl Istanbul

11:45 - 19:25ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

38h 40m2 stops Istanbul Singapore Changi

$2,092Turkish Airlines

Wed, 7 Oct - Thu, 12 Nov

10:20 - 20:12SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

25h 52m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

07:05 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

33h 30m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl

$3,000Air Canada

Wed, 7 Oct - Thu, 12 Nov

10:20 - 07:51SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

37h 31m3 stops Vancouver Intl Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

08:45 - 08:20ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 35m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl

$3,000Air Canada

Mon, 5 Oct - Mon, 19 Oct

10:10 - 16:51SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 41m1 stop Los Angeles

18:55 - 08:05ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 10m1 stop Los Angeles

$6,442Qantas Airways

Mon, 5 Oct - Tue, 13 Oct

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Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific deals on Sydney to Chicago flight tickets

Cathay Pacific

27 Oct

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD13:30Chicago O'Hare Intl

26 Nov

ORD14:10Chicago O'Hare Intl

29h 50m

1 stop

SYD13:00Sydney Kingsford Smith

$1,817

Cathay Pacific

2 Nov

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD12:30Chicago O'Hare Intl

23 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,821

Cathay Pacific

6 Nov

SYD22:20Sydney Kingsford Smith

31h 10m

1 stop

ORD12:30Chicago O'Hare Intl

23 Nov

ORD14:10Chicago O'Hare Intl

26h 25m

1 stop

SYD09:35Sydney Kingsford Smith

$1,858

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

10 Nov

SYD07:30Sydney Kingsford Smith

31h 30m

2 stops

ORD22:00Chicago O'Hare Intl

17 Nov

ORD09:21Chicago O'Hare Intl

30h 14m

2 stops

SYD08:35Sydney Kingsford Smith

$1,699

Air New Zealand

6 Nov

SYD14:05Sydney Kingsford Smith

27h 54m

2 stops

ORD00:59Chicago O'Hare Intl

23 Nov

ORD15:00Chicago O'Hare Intl

24h 35m

2 stops

SYD08:35Sydney Kingsford Smith

$1,745

Air New Zealand

4 Nov

SYD09:55Sydney Kingsford Smith

29h 34m

2 stops

ORD22:29Chicago O'Hare Intl

12 Nov

ORD12:42Chicago O'Hare Intl

26h 53m

2 stops

SYD08:35Sydney Kingsford Smith

$1,759

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 10/11

11:10-16:00

2 stops21h 50m

Chicago O'Hare Intl

Wed 25/11

13:44-09:00

2 stops26h 16m

$1,060

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 10/11

11:10-16:05

1 stop21h 55m

Chicago O'Hare Intl

Sat 21/11

22:03-09:00

1 stop41h 57m

$1,060

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 6/11

11:10-16:05

1 stop21h 55m

Chicago O'Hare Intl

Mon 23/11

08:29-09:00

1 stop31h 31m

$1,150

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 6/11

11:10-22:30

1 stop28h 20m

Chicago O'Hare Intl

Mon 23/11

15:21-09:00

2 stops24h 39m

$1,211

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 2/11

14:00-05:13

3 stops32h 13m

Chicago O'Hare Intl

Mon 23/11

11:35-12:35

3 stops32h 00m

$1,412

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 16/10

14:15-05:16

3 stops31h 01m

Chicago O'Hare Intl

Sat 31/10

06:30-12:35

3 stops38h 05m

$1,578

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 6/11

14:05-00:59

2 stops27h 54m

Chicago O'Hare Intl

Mon 23/11

15:00-08:35

2 stops24h 35m

$1,745

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

09:55-22:29

2 stops29h 34m

Chicago O'Hare Intl

Thu 12/11

12:42-08:35

2 stops26h 53m

$1,759

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 27/10

10:20-19:52

2 stops25h 32m

Chicago O'Hare Intl

Thu 26/11

07:05-09:35

3 stops33h 30m

$2,642

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 26/10

10:20-19:52

2 stops25h 32m

Chicago O'Hare Intl

Sat 31/10

07:05-08:35

3 stops33h 30m

$2,685

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 low for flights on this route.

Typical prices usually range from $1,403 to $1,595.
The lowest price recently found on this route was $1,060.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in October, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,647.

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 $2,085 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 $1,256 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 23% 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 October 2026, prices for Sydney to Chicago flights are approximately 79% 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	$632
Fastest flight time	20h 12m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $632. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,060.

The fastest flight from Sydney to Chicago takes 20h 12m

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. 20h 12m 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 October 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 (31% of total bookings). The next most popular airlines are United Airlines (23%), Air Canada (18%), and American Airlines (13%).

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 $961	Free cancellation	Rating 7.1 11,707 reviews	Search Air Canada flights
Air New Zealand	PriceFrom $1,359	Free cancellation	Rating 8.0 670 reviews	Search Air New Zealand flights
American Airlines	PriceFrom $1,360	Free cancellation	Rating 7.0 12,097 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,420	Free cancellation	Rating 7.4 10,270 reviews	Search United Airlines flights
Qantas Airways	PriceFrom $1,515	Free cancellation	Rating 7.5 1,101 reviews	Search Qantas Airways 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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Complete your trip

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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 $632

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 3/12. 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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Cathay Pacific flights from Sydney to Chicago

Our best Cathay Pacific 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

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

Complete your trip to Chicago

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According to popular flight searches on momondo this year