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

Flights via Houston (IAH) offer the lowest average return price of $1,502.

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 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 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 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 airport is the most popular for stopovers for flights between Sydney and Chicago?

Los Angeles (LAX) was the most common stop: 38% of momondo users choosing one-stop flights on this route connected there.

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 May 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.

$781 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 $2,021 to $1,197. The lowest price recently found on this route was $1,496.

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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 - 16:45

SYD

ORD

22h 35m

1 stop

19:01 - 07:05

ORD

SYD

21h 04m

1 stop

$1,496American Airlines

Thu, 10 Sep - Thu, 24 Sep

09:10 - 18:35

SYD

ORD

24h 25m

2 stops

17:09 - 07:05

ORD

SYD

22h 56m

2 stops

$1,497American Airlines

Thu, 3 Sep - Sat, 12 Sep

13:15 - 05:07

SYD

ORD

30h 52m

3 stops

07:20 - 11:50

ORD

SYD

37h 30m

3 stops

$1,498Multiple Airlines

Wed, 10 Jun - Tue, 23 Jun

09:10 - 00:29

SYD

ORD

30h 19m

1 stop

20:25 - 07:30

ORD

SYD

43h 05m

1 stop

$1,505American Airlines

Thu, 1 Oct - Fri, 9 Oct

09:10 - 12:15

SYD

ORD

42h 05m

1 stop

20:25 - 07:30

ORD

SYD

43h 05m

1 stop

$1,507American Airlines

Thu, 1 Oct - Fri, 9 Oct

09:10 - 16:45

SYD

ORD

22h 35m

1 stop

15:52 - 07:05

ORD

SYD

24h 13m

1 stop

$1,508Qantas Airways

Thu, 10 Sep - Thu, 24 Sep

09:15 - 18:31

SYD

MDW

24h 16m

2 stops

13:05 - 06:50

MDW

SYD

26h 45m

2 stops

$1,522Delta

Thu, 10 Sep - Thu, 24 Sep

09:15 - 21:34

SYD

ORD

27h 19m

2 stops

15:50 - 06:50

ORD

SYD

24h 00m

2 stops

$1,522Delta

Thu, 10 Sep - Thu, 24 Sep

10:15 - 18:37

SYD

MDW

24h 22m

2 stops

13:00 - 07:30

MDW

SYD

26h 30m

2 stops

$1,523Delta

Mon, 19 Oct - Sat, 31 Oct

12:00 - 14:12

SYD

MDW

41h 12m

1 stop

16:10 - 11:50

MDW

SYD

28h 40m

2 stops

$2,326Multiple Airlines

Wed, 3 Jun - Sat, 13 Jun

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets

American Airlines

10 Sept

SYD09:10Sydney Kingsford Smith

22h 35m

1 stop

ORD16:45Chicago O'Hare Intl

24 Sept

ORD19:01Chicago O'Hare Intl

21h 04m

1 stop

SYD07:05Sydney Kingsford Smith

$1,496

American Airlines

3 Sept

SYD09:10Sydney Kingsford Smith

24h 25m

2 stops

ORD18:35Chicago O'Hare Intl

12 Sept

ORD17:09Chicago O'Hare Intl

22h 56m

2 stops

SYD07:05Sydney Kingsford Smith

$1,497

American Airlines

1 Oct

SYD09:10Sydney Kingsford Smith

30h 19m

1 stop

ORD00:29Chicago O'Hare Intl

9 Oct

ORD20:25Chicago O'Hare Intl

43h 05m

1 stop

SYD07:30Sydney Kingsford Smith

$1,505

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

10 Sept

SYD09:10Sydney Kingsford Smith

22h 35m

1 stop

ORD16:45Chicago O'Hare Intl

24 Sept

ORD15:52Chicago O'Hare Intl

24h 13m

1 stop

SYD07:05Sydney Kingsford Smith

$1,508

Qantas Airways

11 Aug

SYD06:00Sydney Kingsford Smith

25h 44m

2 stops

ORD16:44Chicago O'Hare Intl

22 Aug

ORD15:21Chicago O'Hare Intl

28h 09m

2 stops

SYD10:30Sydney Kingsford Smith

$1,760

Qantas Airways

7 Aug

SYD06:25Sydney Kingsford Smith

25h 19m

2 stops

ORD16:44Chicago O'Hare Intl

24 Aug

ORD17:15Chicago O'Hare Intl

25h 30m

2 stops

SYD09:45Sydney Kingsford Smith

$1,912

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 10/9

09:10-16:45

1 stop22h 35m

Chicago O'Hare Intl

Thu 24/9

19:01-07:05

1 stop21h 04m

$1,496

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 3/9

09:10-18:35

2 stops24h 25m

Chicago O'Hare Intl

Sat 12/9

17:09-07:05

2 stops22h 56m

$1,497

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/6

13:15-05:07

3 stops30h 52m

Chicago O'Hare Intl

Tue 23/6

07:20-11:50

3 stops37h 30m

$1,498

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:10-00:29

1 stop30h 19m

Chicago O'Hare Intl

Fri 9/10

20:25-07:30

1 stop43h 05m

$1,505

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:10-12:15

1 stop42h 05m

Chicago O'Hare Intl

Fri 9/10

20:25-07:30

1 stop43h 05m

$1,507

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 10/9

09:10-16:45

1 stop22h 35m

Chicago O'Hare Intl

Thu 24/9

15:52-07:05

1 stop24h 13m

$1,508

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:31

2 stops24h 16m

Chicago Midway

Thu 24/9

13:05-06:50

2 stops26h 45m

$1,522

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 10/9

09:15-21:34

2 stops27h 19m

Chicago O'Hare Intl

Thu 24/9

15:50-06:50

2 stops24h 00m

$1,522

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 19/10

10:15-18:37

2 stops24h 22m

Chicago Midway

Sat 31/10

13:00-07:30

2 stops26h 30m

$1,523

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 3/6

12:00-14:12

1 stop41h 12m

Chicago Midway

Sat 13/6

16:10-11:50

2 stops28h 40m

$2,326

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 $867.

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 $1,826 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 $1,364 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 34% 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 May 2026, prices for Sydney to Chicago flights are approximately 9% 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	22h 33m
Direct flights	None

The fastest flight from Sydney to Chicago takes 22h 33m

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 33m 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 May 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 (30% of total bookings). The next most popular airlines are Air Canada (23%), United Airlines (21%), 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 $1,047	Free cancellation	Rating 7.1 11,011 reviews	Search Air Canada flights
American Airlines	PriceFrom $1,078	Free cancellation	Rating 7.1 11,668 reviews	Search American Airlines flights
Qantas Airways	PriceFrom $1,220	Free cancellation	Rating 7.5 1,033 reviews	Search Qantas Airways flights
Air New Zealand	PriceFrom $1,308	Free cancellation	Rating 8.0 640 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,367	Free cancellation	Rating 7.4 9,695 reviews	Search United Airlines flights
ANA	PriceFrom $1,452	Free cancellation	Rating 8.3 1,207 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Mon 8/6

Mon 15/6

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Sydney

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Sydney to Chicago from $781

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 25/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Sydney to Chicago

Cheap return flights

Cheap one-way flights

Cheap last-minute flights

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

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

Fly to other destinations from Sydney

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year