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

Flights via Vancouver (YVR) offer the lowest average return price of $1,378.

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, American Airlines 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 49% 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.

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: 47% 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.

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 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.

$614 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

Return

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

11:20 - 22:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

28h 35m1 stop Los Angeles

18:46 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

21h 14m1 stop Los Angeles

$1,048American Airlines

Thu, 18 Feb - Mon, 22 Feb

09:15 - 16:37SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

46h 22m2 stops Los Angeles Atlanta Hartsfield-Jackson

17:55 - 06:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

45h 55m2 stops Atlanta Hartsfield-Jackson Los Angeles

$1,054Delta

Mon, 26 Apr - Sat, 8 May

10:40 - 23:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 15m1 stop Los Angeles

07:45 - 08:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 45m1 stop Los Angeles

$1,054Delta

Mon, 16 Nov - Mon, 30 Nov

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

21h 55m1 stop Los Angeles

21:03 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 57m1 stop Los Angeles

$1,079Qantas Airways

Mon, 16 Nov - Mon, 30 Nov

14:05 - 14:18SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

41h 13m1 stop Dallas/Fort Worth

16:59 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

23h 01m1 stop Los Angeles

$1,093Qantas Airways

Thu, 18 Feb - Mon, 22 Feb

11:15 - 16:42SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 27m1 stop Los Angeles

17:15 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

22h 45m1 stop Los Angeles

$1,115Multiple Airlines

Thu, 26 Nov - Thu, 3 Dec

11:10 - 17:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

23h 49m1 stop Los Angeles

17:15 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

22h 45m1 stop Los Angeles

$1,118American Airlines

Mon, 16 Nov - Thu, 3 Dec

11:30 - 16:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

46h 25m1 stop Manila Ninoy Aquino Intl

22:45 - 09:50ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 05m1 stop Manila Ninoy Aquino Intl

$1,460Philippine Airlines

Thu, 19 Nov - Fri, 4 Dec

14:05 - 22:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

24h 55m2 stops Auckland Intl Los Angeles

12:55 - 10:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 40m2 stops Los Angeles Auckland Intl

$1,840Air New Zealand

Thu, 19 Nov - Fri, 4 Dec

07:30 - 20:38SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 08m2 stops Auckland Intl Los Angeles

14:25 - 08:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

25h 10m2 stops San Francisco Auckland Intl

$1,865Air New Zealand

Mon, 1 Feb - Sat, 20 Feb

Cheap last-minute flights

Enter your travel dates to find the best prices.

11:10 - 17:00SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

22h 50m1 stop Los Angeles

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

21h 15m1 stop Los Angeles

$1,046Qantas Airways

Wed, 4 Nov - Wed, 11 Nov

11:10 - 17:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

23h 49m1 stop Los Angeles

21:03 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 57m1 stop Los Angeles

$1,049American Airlines

Mon, 9 Nov - Mon, 23 Nov

11:10 - 12:21SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

42h 11m1 stop Los Angeles

13:26 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 34m2 stops Phoenix Sky Harbor Intl Los Angeles

$1,051American Airlines

Mon, 9 Nov - Mon, 23 Nov

11:10 - 17:59SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

23h 49m1 stop Los Angeles

21:03 - 09:00ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

42h 57m1 stop Los Angeles

$1,051American Airlines

Mon, 9 Nov - Mon, 23 Nov

10:40 - 21:47SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

28h 07m2 stops Los Angeles Salt Lake City

11:19 - 08:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

28h 11m2 stops Detroit Metropolitan Wayne County Los Angeles

$1,054Delta

Mon, 9 Nov - Mon, 23 Nov

10:40 - 23:55SYD Sydney Kingsford Smith-ORD Chicago O'Hare Intl

30h 15m1 stop Los Angeles

14:32 - 08:30ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

24h 58m1 stop Los Angeles

$1,054Delta

Mon, 9 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

12:05 - 12:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 30m3 stops Phoenix Sky Harbor Intl Los Angeles Nadi

$1,554Multiple Airlines

Mon, 9 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

12:05 - 12:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

31h 30m3 stops Phoenix Sky Harbor Intl Los Angeles Nadi

$1,562Multiple Airlines

Mon, 9 Nov - Mon, 23 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

13:57 - 09:35ORD Chicago O'Hare Intl-SYD Sydney Kingsford Smith

26h 38m2 stops Toronto Pearson Intl Vancouver Intl

$3,587Air Canada

Wed, 4 Nov - Wed, 11 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

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

$3,592Air Canada

Wed, 4 Nov - Wed, 11 Nov

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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 Nov

SYD11:10Sydney Kingsford Smith

22h 50m

1 stop

ORD17:00Chicago O'Hare Intl

11 Nov

ORD18:45Chicago O'Hare Intl

21h 15m

1 stop

SYD09:00Sydney Kingsford Smith

$1,046

Qantas Airways

16 Nov

SYD11:10Sydney Kingsford Smith

21h 55m

1 stop

ORD16:05Chicago O'Hare Intl

30 Nov

ORD21:03Chicago O'Hare Intl

42h 57m

1 stop

SYD09:00Sydney Kingsford Smith

$1,079

Qantas Airways

18 Feb

SYD14:05Sydney Kingsford Smith

41h 13m

1 stop

ORD14:18Chicago O'Hare Intl

22 Feb

ORD16:59Chicago O'Hare Intl

23h 01m

1 stop

SYD09:00Sydney Kingsford Smith

$1,093

Delta flights from Sydney to Chicago

Our best Delta deals on Sydney to Chicago flight tickets

Delta

9 Nov

SYD10:40Sydney Kingsford Smith

30h 15m

1 stop

ORD23:55Chicago O'Hare Intl

23 Nov

ORD14:32Chicago O'Hare Intl

24h 58m

1 stop

SYD08:30Sydney Kingsford Smith

$1,054

Delta

20 Jan

SYD10:40Sydney Kingsford Smith

20h 13m

1 stop

ORD13:53Chicago O'Hare Intl

31 Jan

ORD12:42Chicago O'Hare Intl

25h 08m

2 stops

SYD06:50Sydney Kingsford Smith

$1,055

Delta

9 Nov

SYD10:40Sydney Kingsford Smith

24h 50m

2 stops

ORD18:30Chicago O'Hare Intl

23 Nov

ORD08:29Chicago O'Hare Intl

31h 01m

2 stops

SYD08:30Sydney Kingsford Smith

$1,056

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

Thu 18/2

11:20-22:55

1 stop28h 35m

Chicago O'Hare Intl

Mon 22/2

18:46-09:00

1 stop21h 14m

$1,048

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 26/4

09:15-16:37

2 stops46h 22m

Chicago O'Hare Intl

Sat 8/5

17:55-06:50

2 stops45h 55m

$1,054

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 16/11

10:40-23:55

1 stop30h 15m

Chicago O'Hare Intl

Mon 30/11

07:45-08:30

1 stop31h 45m

$1,054

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 16/11

11:10-16:05

1 stop21h 55m

Chicago O'Hare Intl

Mon 30/11

21:03-09:00

1 stop42h 57m

$1,079

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 18/2

14:05-14:18

1 stop41h 13m

Chicago O'Hare Intl

Mon 22/2

16:59-09:00

1 stop23h 01m

$1,093

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 26/11

11:15-16:42

1 stop22h 27m

Chicago O'Hare Intl

Thu 3/12

17:15-09:00

1 stop22h 45m

$1,115

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 16/11

11:10-17:59

1 stop23h 49m

Chicago O'Hare Intl

Thu 3/12

17:15-09:00

1 stop22h 45m

$1,118

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 19/11

11:30-16:55

1 stop46h 25m

Chicago O'Hare Intl

Fri 4/12

22:45-09:50

1 stop42h 05m

$1,460

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 19/11

14:05-22:00

2 stops24h 55m

Chicago O'Hare Intl

Fri 4/12

12:55-10:35

2 stops28h 40m

$1,840

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 1/2

07:30-20:38

2 stops30h 08m

Chicago O'Hare Intl

Sat 20/2

14:25-08:35

2 stops25h 10m

$1,865

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 $1,133 to $1,905.
The lowest price recently found on this route was $1,048.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in October, then you should wait until November to fly from Sydney, when ticket prices are also cheap, with an average price of $1,617.

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 $2,090 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 $1,247 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 43% 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 2026, prices for Sydney to Chicago flights are approximately 40% 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	$614
Fastest flight time	22h 50m
Direct flights	None

The best one-way flight to Chicago from Sydney in the past 72 hours is $614. The best return flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,048.

The fastest flight from Sydney to Chicago takes 22h 50m

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. 22h 50m 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 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 (16%).

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 $954	Free cancellation	Rating 7.1 11,847 reviews	Search Air Canada flights
American Airlines	PriceFrom $962	Free cancellation	Rating 7.0 12,229 reviews	Search American Airlines flights
Delta	PriceFrom $1,054	Free cancellation	Rating 7.8 8,696 reviews	Search Delta flights
Air New Zealand	PriceFrom $1,348	Free cancellation	Rating 8.0 681 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,409	Free cancellation	Rating 7.3 10,460 reviews	Search United Airlines flights
Qantas Airways	PriceFrom $1,504	Free cancellation	Rating 7.5 1,122 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 $614

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 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Sydney to Chicago

Cheap return flights

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Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Delta flights from Sydney to Chicago

Our best Delta 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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