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 37% 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 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: 37% 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 Houston (IAH) have the shortest average one-way travel time: 19h 51m.

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

Flights via Houston (IAH) offer the lowest average return price of $1,543.

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 June 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.

$890 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 $2,123 to $1,603. The lowest price recently found on this route was $1,437.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Sydney to Chicago

Round-trip

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

09:10 - 18:05

SYD

ORD

23h 55m

1 stop

13:50 - 07:05

ORD

SYD

26h 15m

1 stop

$1,437American Airlines

Tue, 22 Sep - Tue, 29 Sep

09:10 - 18:03

SYD

ORD

23h 53m

2 stops

16:53 - 06:55

ORD

SYD

22h 02m

1 stop

$1,448American Airlines

Wed, 23 Sep - Tue, 6 Oct

12:00 - 20:00

SYD

ORD

23h 00m

2 stops

20:55 - 06:55

ORD

SYD

42h 00m

1 stop

$1,458American Airlines

Mon, 21 Sep - Sat, 10 Oct

06:00 - 20:00

SYD

ORD

29h 00m

2 stops

20:55 - 06:55

ORD

SYD

42h 00m

1 stop

$1,481American Airlines

Thu, 24 Sep - Sat, 10 Oct

10:10 - 16:03

SYD

ORD

21h 53m

1 stop

18:03 - 08:00

ORD

SYD

21h 57m

1 stop

$1,501American Airlines

Tue, 6 Oct - Sat, 31 Oct

09:10 - 18:03

SYD

ORD

23h 53m

2 stops

18:03 - 08:05

ORD

SYD

22h 02m

1 stop

$1,508American Airlines

Sat, 3 Oct - Tue, 20 Oct

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

09:28 - 22:10

ORD

SYD

45h 42m

3 stops

$1,515Multiple Airlines

Sat, 25 Jul - Sat, 1 Aug

09:15 - 23:59

SYD

ORD

29h 44m

2 stops

11:30 - 07:50

ORD

SYD

28h 20m

2 stops

$1,525Delta

Thu, 1 Oct - Fri, 16 Oct

09:15 - 18:33

SYD

MDW

24h 18m

2 stops

13:00 - 07:50

MDW

SYD

26h 50m

2 stops

$1,535Delta

Sat, 3 Oct - Tue, 20 Oct

09:15 - 18:33

SYD

MDW

24h 18m

2 stops

14:00 - 06:50

MDW

SYD

25h 50m

2 stops

$1,914Delta

Mon, 24 Aug - Wed, 9 Sep

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American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

American Airlines

22 Sept

SYD09:10Sydney Kingsford Smith

23h 55m

1 stop

ORD18:05Chicago O'Hare Intl

29 Sept

ORD13:50Chicago O'Hare Intl

26h 15m

1 stop

SYD07:05Sydney Kingsford Smith

$1,437

American Airlines

23 Sept

SYD09:10Sydney Kingsford Smith

23h 53m

2 stops

ORD18:03Chicago O'Hare Intl

6 Oct

ORD16:53Chicago O'Hare Intl

22h 02m

1 stop

SYD06:55Sydney Kingsford Smith

$1,448

American Airlines

21 Sept

SYD12:00Sydney Kingsford Smith

23h 00m

2 stops

ORD20:00Chicago O'Hare Intl

10 Oct

ORD20:55Chicago O'Hare Intl

42h 00m

1 stop

SYD06:55Sydney Kingsford Smith

$1,458

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

11 Aug

SYD06:25Sydney Kingsford Smith

24h 29m

2 stops

ORD15:54Chicago O'Hare Intl

18 Aug

ORD15:22Chicago O'Hare Intl

31h 33m

2 stops

SYD13:55Sydney Kingsford Smith

$1,691

Qantas Airways

23 July

SYD12:00Sydney Kingsford Smith

21h 16m

1 stop

ORD18:16Chicago O'Hare Intl

30 July

ORD08:10Chicago O'Hare Intl

31h 55m

1 stop

SYD07:05Sydney Kingsford Smith

$1,998

Qantas Airways

11 Aug

SYD09:10Sydney Kingsford Smith

21h 44m

1 stop

ORD15:54Chicago O'Hare Intl

18 Aug

ORD15:22Chicago O'Hare Intl

31h 33m

2 stops

SYD13:55Sydney Kingsford Smith

$2,022

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 22/9

09:10-18:05

1 stop23h 55m

Chicago O'Hare Intl

Tue 29/9

13:50-07:05

1 stop26h 15m

$1,437

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 23/9

09:10-18:03

2 stops23h 53m

Chicago O'Hare Intl

Tue 6/10

16:53-06:55

1 stop22h 02m

$1,448

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 21/9

12:00-20:00

2 stops23h 00m

Chicago O'Hare Intl

Sat 10/10

20:55-06:55

1 stop42h 00m

$1,458

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 24/9

06:00-20:00

2 stops29h 00m

Chicago O'Hare Intl

Sat 10/10

20:55-06:55

1 stop42h 00m

$1,481

Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 6/10

10:10-16:03

1 stop21h 53m

Chicago O'Hare Intl

Sat 31/10

18:03-08:00

1 stop21h 57m

$1,501

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 3/10

09:10-18:03

2 stops23h 53m

Chicago O'Hare Intl

Tue 20/10

18:03-08:05

1 stop22h 02m

$1,508

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 25/7

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Sat 1/8

09:28-22:10

3 stops45h 42m

$1,515

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:15-23:59

2 stops29h 44m

Chicago O'Hare Intl

Fri 16/10

11:30-07:50

2 stops28h 20m

$1,525

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 3/10

09:15-18:33

2 stops24h 18m

Chicago Midway

Tue 20/10

13:00-07:50

2 stops26h 50m

$1,535

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 24/8

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 9/9

14:00-06:50

2 stops25h 50m

$1,914

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 $890.

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 $1,891 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 2% 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 June 2026, prices for Sydney to Chicago flights are approximately 27% 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

Fastest flight time	19h 30m
Direct flights	None

The fastest flight from Sydney to Chicago takes 19h 30m

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. 19h 30m 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 June 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 (26% of total bookings). The next most popular airlines are Air Canada (23%), United Airlines (21%), and Air New Zealand (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 $1,075	Free cancellation	Rating 7.1 11,154 reviews	Search Air Canada flights
Qantas Airways	PriceFrom $1,253	Free cancellation	Rating 7.5 1,046 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,254	Free cancellation	Rating 7.1 11,635 reviews	Search American Airlines flights
Air New Zealand	PriceFrom $1,343	Free cancellation	Rating 8.0 645 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,404	Free cancellation	Rating 7.4 9,804 reviews	Search United Airlines flights
ANA	PriceFrom $1,518	Free cancellation	Rating 8.3 1,230 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

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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 $890

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 7/9. 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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American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

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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.

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Popular flights according to clicks in the last 7 days on momondo

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