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

Flights via Houston (IAH) offer the lowest average return price of $1,562.

Which airlines fly to Chicago?

Qantas Airways, Air Canada and Air New Zealand 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 40% 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.

Which stopover airport has the shortest travel time from Sydney to Chicago?

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 19h 51m.

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

Etihad Airways 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: 43% 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 July 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.

$999 Cheap Flights from Sydney to Chicago in 2026

Q: 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 $1,564 to $2,397. The lowest price recently found on this route was $1,290.

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.

06:05 - 06:17

SYD

ORD

39h 12m

2 stops

09:20 - 11:50

ORD

SYD

35h 30m

3 stops

$1,290Multiple Airlines

Wed, 12 Aug - Wed, 19 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

11:06 - 22:25

MDW

SYD

44h 19m

3 stops

$1,346Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

11:06 - 22:25

MDW

SYD

44h 19m

3 stops

$1,380Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

06:15 - 06:17

SYD

ORD

39h 02m

2 stops

07:29 - 11:50

ORD

SYD

37h 21m

3 stops

$1,389Multiple Airlines

Mon, 27 Jul - Tue, 11 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

06:05 - 22:25

MDW

SYD

49h 20m

3 stops

$1,395Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

10:16 - 22:25

ORD

SYD

45h 09m

3 stops

$1,419Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

10:30 - 07:54

SYD

ORD

37h 24m

2 stops

16:05 - 07:55

ORD

SYD

23h 50m

1 stop

$1,573United Airlines

Tue, 13 Oct - Wed, 14 Oct

10:40 - 22:10

SYD

MDW

28h 30m

2 stops

13:05 - 08:30

MDW

SYD

26h 25m

2 stops

$2,443Delta

Mon, 7 Dec - Tue, 29 Dec

10:40 - 16:20

SYD

MDW

22h 40m

2 stops

13:05 - 08:30

MDW

SYD

26h 25m

2 stops

$2,444Delta

Wed, 4 Nov - Wed, 11 Nov

10:15 - 16:39

SYD

MDW

22h 24m

2 stops

09:59 - 07:50

MDW

SYD

29h 51m

2 stops

$2,479Delta

Sat, 10 Oct - Mon, 19 Oct

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Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

8 Aug

SYD06:25Sydney Kingsford Smith

32h 36m

2 stops

ORD00:01Chicago O'Hare Intl

19 Aug

ORD17:16Chicago O'Hare Intl

26h 29m

2 stops

SYD10:45Sydney Kingsford Smith

$1,753

Qantas Airways

6 Aug

SYD06:25Sydney Kingsford Smith

32h 05m

2 stops

ORD23:30Chicago O'Hare Intl

19 Aug

ORD15:22Chicago O'Hare Intl

28h 08m

2 stops

SYD10:30Sydney Kingsford Smith

$1,754

Qantas Airways

22 July

SYD06:25Sydney Kingsford Smith

31h 35m

2 stops

ORD23:00Chicago O'Hare Intl

23 Aug

ORD10:30Chicago O'Hare Intl

32h 15m

2 stops

SYD09:45Sydney Kingsford Smith

$1,878

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

6 Aug

SYD11:55Sydney Kingsford Smith

35h 04m

2 stops

ORD07:59Chicago O'Hare Intl

19 Aug

ORD15:35Chicago O'Hare Intl

28h 05m

2 stops

SYD10:40Sydney Kingsford Smith

$1,751

Air New Zealand

12 Aug

SYD09:55Sydney Kingsford Smith

30h 04m

2 stops

ORD00:59Chicago O'Hare Intl

19 Aug

ORD15:35Chicago O'Hare Intl

28h 05m

2 stops

SYD10:40Sydney Kingsford Smith

$1,757

Air New Zealand

25 Aug

SYD11:55Sydney Kingsford Smith

28h 04m

2 stops

ORD00:59Chicago O'Hare Intl

17 Nov

ORD12:40Chicago O'Hare Intl

26h 55m

2 stops

SYD08:35Sydney Kingsford Smith

$1,773

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/8

06:05-06:17

2 stops39h 12m

Chicago O'Hare Intl

Wed 19/8

09:20-11:50

3 stops35h 30m

$1,290

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

11:06-22:25

3 stops44h 19m

$1,346

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

11:06-22:25

3 stops44h 19m

$1,380

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 27/7

06:15-06:17

2 stops39h 02m

Chicago O'Hare Intl

Tue 11/8

07:29-11:50

3 stops37h 21m

$1,389

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

06:05-22:25

3 stops49h 20m

$1,395

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 3/8

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Mon 10/8

10:16-22:25

3 stops45h 09m

$1,419

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 13/10

10:30-07:54

2 stops37h 24m

Chicago O'Hare Intl

Wed 14/10

16:05-07:55

1 stop23h 50m

$1,573

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 7/12

10:40-22:10

2 stops28h 30m

Chicago Midway

Tue 29/12

13:05-08:30

2 stops26h 25m

$2,443

Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 4/11

10:40-16:20

2 stops22h 40m

Chicago Midway

Wed 11/11

13:05-08:30

2 stops26h 25m

$2,444

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 10/10

10:15-16:39

2 stops22h 24m

Chicago Midway

Mon 19/10

09:59-07:50

2 stops29h 51m

$2,479

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 December, then you should wait until August to fly from Sydney, when ticket prices are also cheap, with an average price of $901.

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 $1,968 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 $1,477 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 July 2026, prices for Sydney to Chicago flights are approximately 73% 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

Fastest flight time	22h 24m
Direct flights	None

The fastest flight from Sydney to Chicago takes 22h 24m

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

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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 24m 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 July 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 (27% of total bookings). The next most popular airlines are Air Canada (24%), United Airlines (23%), and Air New Zealand (11%).

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 $1,089	Free cancellation	Rating 7.1 11,328 reviews	Search Air Canada flights
Qantas Airways	PriceFrom $1,269	Free cancellation	Rating 7.5 1,061 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,270	Free cancellation	Rating 7.1 11,805 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,422	Free cancellation	Rating 7.4 9,979 reviews	Search United Airlines flights
Air New Zealand	PriceFrom $1,431	Free cancellation	Rating 8.0 653 reviews	Search Air New Zealand flights
ANA	PriceFrom $1,537	Free cancellation	Rating 8.3 1,271 reviews	Search ANA 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 $999

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 18/8. 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

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

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago

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

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