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 and Philippine Airlines are the most popular carriers operating from Sydney Kingsford Smith to Chicago

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

Flights via Houston (IAH) offer the lowest average return price of $1,550.

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 5 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 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: 45% 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 5 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.

$611 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 $1,449 to $2,139. The lowest price recently found on this route was $1,315.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Sydney to Chicago

Return

One-way

Cheap return flights

Enter your travel dates to find the best prices.

13:15 - 10:58

SYD

MDW

36h 43m

3 stops

07:25 - 11:50

MDW

SYD

37h 25m

3 stops

$1,315Multiple Airlines

Wed, 9 Sep - Sun, 13 Sep

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

09:20 - 22:25

ORD

SYD

46h 05m

3 stops

$1,452Multiple Airlines

Tue, 4 Aug - Tue, 11 Aug

13:15 - 09:51

SYD

MDW

35h 36m

3 stops

06:05 - 11:50

MDW

SYD

38h 45m

3 stops

$1,474Multiple Airlines

Thu, 6 Aug - Wed, 19 Aug

13:15 - 06:17

SYD

ORD

32h 02m

2 stops

09:20 - 11:50

ORD

SYD

35h 30m

3 stops

$1,475Multiple Airlines

Wed, 5 Aug - Wed, 19 Aug

13:15 - 09:51

SYD

MDW

35h 36m

3 stops

11:45 - 22:25

MDW

SYD

43h 40m

3 stops

$1,485Multiple Airlines

Fri, 7 Aug - Sat, 22 Aug

21:35 - 16:00

SYD

ORD

34h 25m

1 stop

20:20 - 06:30

ORD

SYD

41h 10m

1 stop

$1,608Etihad Airways

Sat, 24 Oct - Sun, 1 Nov

16:50 - 15:00

SYD

ORD

39h 10m

1 stop

20:20 - 17:45

ORD

SYD

28h 25m

1 stop

$1,642Etihad Airways

Wed, 18 Nov - Wed, 25 Nov

09:15 - 18:19

SYD

MDW

24h 04m

2 stops

13:00 - 07:50

MDW

SYD

26h 50m

2 stops

$2,437Delta

Mon, 14 Sep - Tue, 6 Oct

09:15 - 18:19

SYD

MDW

24h 04m

2 stops

13:00 - 06:50

MDW

SYD

26h 50m

2 stops

$2,438Delta

Thu, 10 Sep - Wed, 23 Sep

10:15 - 16:39

SYD

MDW

22h 24m

2 stops

09:29 - 08:30

MDW

SYD

30h 01m

2 stops

$2,481Delta

Sat, 24 Oct - Sun, 1 Nov

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

Etihad Airways flights from Sydney to Chicago

Our best Etihad Airways deals on Sydney to Chicago flight tickets

Etihad Airways

24 Oct

SYD21:35Sydney Kingsford Smith

34h 25m

1 stop

ORD16:00Chicago O'Hare Intl

1 Nov

ORD20:20Chicago O'Hare Intl

41h 10m

1 stop

SYD06:30Sydney Kingsford Smith

$1,608

Etihad Airways

18 Nov

SYD16:50Sydney Kingsford Smith

39h 10m

1 stop

ORD15:00Chicago O'Hare Intl

25 Nov

ORD20:20Chicago O'Hare Intl

28h 25m

1 stop

SYD17:45Sydney Kingsford Smith

$1,642

Etihad Airways

13 Nov

SYD16:50Sydney Kingsford Smith

32h 05m

1 stop

ORD07:55Chicago O'Hare Intl

20 Nov

ORD13:10Chicago O'Hare Intl

48h 20m

1 stop

SYD06:30Sydney Kingsford Smith

$1,752

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

8 Sept

SYD11:55Sydney Kingsford Smith

28h 04m

2 stops

ORD00:59Chicago O'Hare Intl

22 Sept

ORD16:11Chicago O'Hare Intl

27h 29m

2 stops

SYD10:40Sydney Kingsford Smith

$1,679

Air New Zealand

8 Sept

SYD09:55Sydney Kingsford Smith

28h 10m

2 stops

ORD23:05Chicago O'Hare Intl

22 Sept

ORD16:30Chicago O'Hare Intl

25h 15m

2 stops

SYD08:45Sydney Kingsford Smith

$1,749

Air New Zealand

19 Aug

SYD09:55Sydney Kingsford Smith

28h 31m

2 stops

ORD23:26Chicago O'Hare Intl

26 Aug

ORD14:35Chicago O'Hare Intl

27h 10m

2 stops

SYD08:45Sydney Kingsford Smith

$1,769

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/9

13:15-10:58

3 stops36h 43m

Chicago Midway

Sun 13/9

07:25-11:50

3 stops37h 25m

$1,315

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 4/8

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Tue 11/8

09:20-22:25

3 stops46h 05m

$1,452

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

13:15-09:51

3 stops35h 36m

Chicago Midway

Wed 19/8

06:05-11:50

3 stops38h 45m

$1,474

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 5/8

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Wed 19/8

09:20-11:50

3 stops35h 30m

$1,475

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 7/8

13:15-09:51

3 stops35h 36m

Chicago Midway

Sat 22/8

11:45-22:25

3 stops43h 40m

$1,485

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 24/10

21:35-16:00

1 stop34h 25m

Chicago O'Hare Intl

Sun 1/11

20:20-06:30

1 stop41h 10m

$1,608

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 18/11

16:50-15:00

1 stop39h 10m

Chicago O'Hare Intl

Wed 25/11

20:20-17:45

1 stop28h 25m

$1,642

Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 14/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 6/10

13:00-07:50

2 stops26h 50m

$2,437

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 23/9

13:00-06:50

2 stops26h 50m

$2,438

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 24/10

10:15-16:39

2 stops22h 24m

Chicago Midway

Sun 1/11

09:29-08:30

2 stops30h 01m

$2,481

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 September, then you should wait until October to fly from Sydney, when ticket prices are also cheap, with an average price of $1,524.

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 $1,954 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 $1,465 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 17% 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 12% 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	23h 10m
Direct flights	None

The fastest flight from Sydney to Chicago takes 23h 10m

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. 23h 10m 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 5 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 (28% 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 $1,081	Free cancellation	Rating 7.1 11,371 reviews	Search Air Canada flights
Qantas Airways	PriceFrom $1,259	Free cancellation	Rating 7.5 1,066 reviews	Search Qantas Airways flights
American Airlines	PriceFrom $1,260	Free cancellation	Rating 7.1 11,834 reviews	Search American Airlines flights
United Airlines	PriceFrom $1,411	Free cancellation	Rating 7.4 10,020 reviews	Search United Airlines flights
Air New Zealand	PriceFrom $1,420	Free cancellation	Rating 8.0 654 reviews	Search Air New Zealand 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

Fri 21/8

Fri 28/8

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 $611

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.

Find the cheapest flights from Sydney to Chicago

Cheap return flights

Cheap one-way flights

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

Etihad Airways flights from Sydney to Chicago

Our best Etihad 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

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