How long is the flight from Sydney to Chicago?

Airlines like Cathay Pacific fly from Sydney to Chicago in about 38h 15m. The time it takes to get you to your destination can typically vary by up to . The distance between Sydney and Chicago is about 14851 km.

What are the cheapest airlines flying from Sydney to Chicago round-trip?

Cheapflights users have booked flights from Sydney to Chicago round-trip from $947. Other airlines that can offer you cheap pricing are Air New Zealand, from $1,338, and American Airlines, from $1,340. You may be able to fly from Sydney to Chicago for 48% less than the average price by searching for these airlines.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

What are the most popular airlines that fly from Sydney to Chicago?

When booking a flight from Sydney to Chicago, you may want to consider flying on Qantas Airways, Air Canada or Air New Zealand as they are the most popular for this route.

What is the cheapest time of day to fly from SYD to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Sydney to Chicago as you normally would.

What airport do you fly from for flights from Sydney to Chicago?

For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.

Can I find deals for flights from Sydney to Chicago that include hotel bookings?

Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

How can I find direct flights from Sydney to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.

Can I find deals for business class flights from Sydney to Chicago?

Yes. Cheapflights offers flight deals from Sydney to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$983+ Cheap Flights from Sydney to Chicago

Cheap flight deals from Sydney to Chicago

Enter your travel dates to find the best prices.

Cheapest

Best

Last-minute

One-way

Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 September 2026.

Mon 2/1114:00 -

3 stops32h 13m

Mon 9/1106:30 -

3 stops37h 05m

Deal found 18/9$1,284

Thu 5/1114:00 -

3 stops32h 13m

Thu 12/1110:26 -

3 stops33h 09m

Deal found 21/9$1,509

Tue 10/1107:30 -

2 stops31h 30m

Tue 17/1109:21 -

2 stops30h 14m

Deal found 18/9$1,704

Thu 8/1018:50 -

2 stops26h 26m

Sat 24/1006:30 -

2 stops31h 55m

Deal found 19/9$1,784

Thu 5/1114:05 -

2 stops27h 54m

Thu 12/1111:52 -

2 stops27h 43m

Deal found 23/9$1,785

Thu 19/1122:20 -

1 stop31h 10m

Thu 26/1114:10 -

1 stop48h 05m

Deal found 19/9$1,796

Thu 5/1122:20 -

1 stop31h 10m

Thu 12/1114:10 -

1 stop26h 25m

Deal found 21/9$1,798

Tue 10/1115:15 -

1 stop38h 15m

Tue 17/1114:10 -

1 stop26h 25m

Deal found 18/9$1,801

Thu 19/1109:55 -

2 stops30h 31m

Thu 26/1110:25 -

2 stops29h 10m

Deal found 19/9$1,805

Find flight deals from Sydney to Chicago

Round-trip from	$1,509
One-way from	$983
Popular in	May
Cheapest in	October
Average price	$1,785

5/11-12/11
6 total stops
65h 22m total
Sydney to Chicago

Search Deals

Etihad Airways
1/10-31/12
1 total stop
50h 45m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($223 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($70 potential savings vs. average return price).

Search Deals

Average for round-trip flights in September 2026

Search Deals

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

Sat 7/11

21:30-07:55

1 stop51h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,038

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 7/11

18:30-12:30

2 stops35h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,277

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 1/10

15:10-13:55

2 stops37h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,327

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 25/12

21:30-19:25

2 stops38h 55m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,392

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 30/9

15:40-14:20

2 stops37h 40m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,400

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 2/11

15:15-12:30

1 stop38h 15m

Chicago O'Hare Intl

Mon 9/11

14:10-09:35

1 stop26h 25m

$1,808

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 5/11

22:20-12:30

1 stop31h 10m

Chicago O'Hare Intl

Mon 9/11

14:10-20:50

1 stop37h 40m

$1,894

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 19/11

19:45-12:30

2 stops33h 45m

Chicago O'Hare Intl

Thu 26/11

14:10-20:50

1 stop37h 40m

$1,990

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 2/11

21:05-12:30

2 stops32h 25m

Chicago O'Hare Intl

Mon 9/11

14:10-09:35

1 stop26h 25m

$2,000

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 6/11

11:30-05:40

2 stops35h 10m

Chicago O'Hare Intl

Fri 13/11

22:45-09:50

1 stop42h 05m

$2,016

Flights are sorted by cheapest return flights first.

Deals found on 20/9

Showing 1-10 of 13 resultsSorted by cheapest first

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.

SYD-CHI

SYD-ORD

Estimated return price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Sydney to Chicago

SYD-CHI

SYD-ORD

What is the cheapest month to book a flight from Sydney to Chicago?

Currently, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,489). Flying from Sydney to Chicago in May is currently the most expensive (average of $2,026). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost for a return flight from Sydney to Chicago?

Airfare is typical for this route at the moment.

Sydney to Chicago flights typically cost between $1,277 and $2,033 in November.
The cheapest return price found within the last 5 days was $1,509 on Multiple Airlines (5 Nov–12 Nov).

What’s the top stopover airport for flights from Sydney to Chicago?

Los Angeles (LAX) – chosen by Cheapflights users on 60% of one-stop itineraries from Sydney to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Sydney to Chicago?

Nadi (NAN) is the most affordable one-stop option, with an average return flight price of $784.

What’s the fastest stopover option from Sydney to Chicago?

Flights via Nadi (NAN) have the shortest average one-way travel time for one-stop routes: 16h 57m.

Which airport typically offers the quickest stopover for flights from Sydney to Chicago?

Flights via Houston (IAH) offer the fastest connection on this route, with an average stopover time of 1h 27m.

How far ahead should I book a flight from Sydney to Chicago?

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Chicago

See what other customers who have flown with Air New Zealand,Qantas Airways, andUnited Airlines from Sydney to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Air New Zealand

8.0

Very Good

669 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Qantas Airways

7.5

Good

1,101 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

United Airlines

7.4

Good

10,233 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Air Canada

7.1

Good

11,677 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

American Airlines

7.0

Good

12,075 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Related info for your journey

What airport do you fly from for flights from Sydney to Chicago?
For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.
How long is the flight from Sydney to Chicago?
Airlines like Cathay Pacific fly from Sydney to Chicago in about 38h 15m. The time it takes to get you to your destination can typically vary by up to . The distance between Sydney and Chicago is about 14851 km.
What are the cheapest airlines flying from Sydney to Chicago round-trip?
Cheapflights users have booked flights from Sydney to Chicago round-trip from $947. Other airlines that can offer you cheap pricing are Air New Zealand, from $1,338, and American Airlines, from $1,340. You may be able to fly from Sydney to Chicago for 48% less than the average price by searching for these airlines.
Can I find deals for flights from Sydney to Chicago that include hotel bookings?
Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from Sydney to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.
Can I find deals for business class flights from Sydney to Chicago?
Yes. Cheapflights offers flight deals from Sydney to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,489). Flying from Sydney to Chicago in May is currently the most expensive (average of $2,026). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Airlines

Alternative routes

Chicago flight routes

Complete your trip

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Other flights from Sydney

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Fly from Sydney to Chicago on these airlines

Qantas Airways flights from Sydney Kingsford Smith to Chicago

Air Canada flights from Sydney Kingsford Smith to Chicago

ANA flights from Sydney Kingsford Smith to Chicago

Top 5 airlines flying from Sydney to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	Cheapest$947	Average$1,635	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Air New Zealand	Cheapest$1,338	Average$1,596	FlexibilityNo cancel fee	On-time78%	Search Air New Zealand flights
American Airlines	Cheapest$1,340	Average$1,718	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
United Airlines	Cheapest$1,399	Average$1,782	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Qantas Airways	Cheapest$1,485	Average$1,805	FlexibilityNo cancel fee	On-time74%	Search Qantas Airways flights

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How does Cheapflights help users find flights from Sydney to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Sydney to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Sydney to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Sydney.

Can Cheapflights find flights from Sydney to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Sydney to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?

Of course! You can now track prices for flights from Sydney to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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Cheap flights from Sydney to Chicago from $983

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Sydney to Chicago

Cheapest flights from Sydney to ChicagoExplore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 September 2026.

Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 September 2026.

Best flights from Sydney to ChicagoDiscover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 24 September 2026.

Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 24 September 2026.

Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated 24 September 2026 and is based on user searches.

Discover last-minute flight deals from Sydney to Chicago. Data last updated 24 September 2026 and is based on user searches.

One-way flights from Sydney to ChicagoSearch for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated 24 September 2026.

Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated 24 September 2026.

Find flight deals from Sydney to Chicago

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One-way from

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Cheapest in

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Cheapflights Fare Finder

Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.

Cheapflights Insights

What is the cheapest month to book a flight from Sydney to Chicago?

How much does it cost for a return flight from Sydney to Chicago?

Airfare is typical for this route at the moment.

Sydney to Chicago flights typically cost between $1,277 and $2,033 in November.The cheapest return price found within the last 5 days was $1,509 on Multiple Airlines (5 Nov–12 Nov).

What’s the top stopover airport for flights from Sydney to Chicago?

Share of one-stop return flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Los Angeles (LAX) – chosen by Cheapflights users on 60% of one-stop itineraries from Sydney to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Sydney to Chicago?

Average return fare for one-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Nadi (NAN) is the most affordable one-stop option, with an average return flight price of $784.

What’s the fastest stopover option from Sydney to Chicago?

Shortest average travel time for one-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via Nadi (NAN) have the shortest average one-way travel time for one-stop routes: 16h 57m.

Which airport typically offers the quickest stopover for flights from Sydney to Chicago?

Average stopover duration for one-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average stopover time of 1h 27m.

How far ahead should I book a flight from Sydney to Chicago?

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Chicago

See what other customers who have flown with Air New Zealand,Qantas Airways, andUnited Airlines from Sydney to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What airport do you fly from for flights from Sydney to Chicago?

How long is the flight from Sydney to Chicago?

What are the cheapest airlines flying from Sydney to Chicago round-trip?

Can I find deals for flights from Sydney to Chicago that include hotel bookings?

How can I find direct flights from Sydney to Chicago?

Can I find deals for business class flights from Sydney to Chicago?

What is the cheapest month to book a flight from Sydney to Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Sydney to Chicago on these airlines

Choose from the following airlines for your flight from Sydney to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 24 September 2026.

Alternative routes for Sydney to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 24 September 2026.

Complete your trip

Complete your trip to Chicago by adding a car hire and/or hotel booking to your travel itinerary.

Direct flights to United States

Book a non-stop flight to one of these other cities located in United States.

Search flights from Sydney to Chicago by cabin class

Find flights from Sydney to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Sydney and Chicago flights

Browse other Sydney and Chicago flight options. Last updated on 24 September 2026.

Other flights from Sydney

Browse through other flights departing from Sydney. Flights are based on user searches made on Cheapflights and were last updated on 24 September 2026.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Top 5 airlines flying from Sydney to Chicago

Fly with Cheapflights

How does Cheapflights help users find flights from Sydney to Chicago?

Why should you use Cheapflights to find cheap flight tickets from Sydney to Chicago?

Can Cheapflights find flights from Sydney to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?

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Travel Smart

Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 September 2026.

Best flights from Sydney to Chicago
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 24 September 2026.

Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated 24 September 2026 and is based on user searches.

One-way flights from Sydney to Chicago
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated 24 September 2026.

Sydney to Chicago flights typically cost between $1,277 and $2,033 in November.
The cheapest return price found within the last 5 days was $1,509 on Multiple Airlines (5 Nov–12 Nov).