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 stopover airport offers the lowest fares from Sydney to Chicago?

Flights via Vancouver (YVR) offer the lowest average return price of $1,144.

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

Air New Zealand and Delta are the most popular carriers operating from Sydney Kingsford Smith to Chicago

Which airlines fly to Chicago?

Qantas Airways, Air Canada and United Airlines 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 51% 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 airport is the most popular for stopovers for flights between Sydney and Chicago?

Los Angeles (LAX) was the most common stop: 54% 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 February 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.

$780 Cheap Flights from Sydney to Chicago in 2026

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Find the cheapest flights from Sydney to Chicago

Round-trip

One-way

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09:55 - 20:23

SYD

ORD

26h 28m

2 stops

14:35 - 10:15

ORD

SYD

27h 40m

2 stops

$1,563Air New Zealand

Tue, 10 Mar - Tue, 17 Mar

21:30 - 20:00

SYD

ORD

38h 30m

2 stops

15:35 - 08:35

ORD

SYD

25h 00m

1 stop

$1,574Multiple Airlines

Tue, 10 Mar - Tue, 17 Mar

09:10 - 16:41

SYD

ORD

22h 31m

1 stop

15:52 - 07:05

ORD

SYD

24h 13m

2 stops

$1,595American Airlines

Mon, 13 Jul - Mon, 10 Aug

09:10 - 14:18

SYD

ORD

20h 08m

1 stop

15:12 - 07:05

ORD

SYD

24h 53m

1 stop

$1,596American Airlines

Mon, 13 Jul - Mon, 10 Aug

06:25 - 15:48

SYD

ORD

24h 23m

2 stops

18:45 - 07:05

ORD

SYD

21h 20m

1 stop

$1,616American Airlines

Mon, 13 Jul - Mon, 10 Aug

17:50 - 07:00

SYD

ORD

28h 10m

1 stop

21:14 - 11:50

ORD

SYD

47h 36m

2 stops

$1,627Multiple Airlines

Fri, 17 Apr - Thu, 23 Apr

10:25 - 08:00

SYD

ORD

37h 35m

2 stops

08:50 - 07:20

ORD

SYD

31h 30m

1 stop

$1,629Air Canada

Thu, 19 Mar - Tue, 21 Apr

10:25 - 08:00

SYD

ORD

37h 35m

2 stops

07:13 - 07:20

ORD

SYD

33h 07m

3 stops

$1,646Air Canada

Thu, 19 Mar - Tue, 21 Apr

09:40 - 18:40

SYD

MDW

25h 00m

2 stops

13:24 - 06:50

MDW

SYD

26h 26m

2 stops

$1,713Delta

Thu, 19 Mar - Tue, 21 Apr

09:15 - 22:28

SYD

MDW

28h 13m

2 stops

14:00 - 06:50

MDW

SYD

25h 50m

2 stops

$1,788Delta

Sat, 2 May - Tue, 16 Jun

Air New Zealand flights from Sydney to Chicago

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

Air New Zealand

10 Mar

SYD09:55Sydney Kingsford Smith

26h 28m

2 stops

ORD20:23Chicago O'Hare Intl

17 Mar

ORD14:35Chicago O'Hare Intl

27h 40m

2 stops

SYD10:15Sydney Kingsford Smith

$1,563

Air New Zealand

19 Mar

SYD11:45Sydney Kingsford Smith

27h 15m

2 stops

ORD23:00Chicago O'Hare Intl

3 Apr

ORD16:00Chicago O'Hare Intl

27h 40m

2 stops

SYD11:40Sydney Kingsford Smith

$1,633

Air New Zealand

13 July

SYD11:55Sydney Kingsford Smith

24h 41m

2 stops

ORD21:36Chicago O'Hare Intl

10 Aug

ORD14:21Chicago O'Hare Intl

27h 24m

2 stops

SYD08:45Sydney Kingsford Smith

$1,709

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets

Qantas Airways

22 June

SYD09:10Sydney Kingsford Smith

27h 40m

1 stop

ORD21:50Chicago O'Hare Intl

19 July

ORD11:49Chicago O'Hare Intl

28h 16m

1 stop

SYD07:05Sydney Kingsford Smith

$1,695

Qantas Airways

13 July

SYD09:10Sydney Kingsford Smith

25h 45m

1 stop

ORD19:55Chicago O'Hare Intl

10 Aug

ORD18:45Chicago O'Hare Intl

21h 20m

1 stop

SYD07:05Sydney Kingsford Smith

$1,703

Qantas Airways

22 June

SYD09:10Sydney Kingsford Smith

29h 49m

1 stop

ORD23:59Chicago O'Hare Intl

19 July

ORD19:00Chicago O'Hare Intl

21h 05m

1 stop

SYD07:05Sydney Kingsford Smith

$1,706

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

09:55-20:23

2 stops26h 28m

Chicago O'Hare Intl

Tue 17/3

14:35-10:15

2 stops27h 40m

$1,563

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

21:30-20:00

2 stops38h 30m

Chicago O'Hare Intl

Tue 17/3

15:35-08:35

1 stop25h 00m

$1,574

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 13/7

09:10-16:41

1 stop22h 31m

Chicago O'Hare Intl

Mon 10/8

15:52-07:05

2 stops24h 13m

$1,595

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 13/7

09:10-14:18

1 stop20h 08m

Chicago O'Hare Intl

Mon 10/8

15:12-07:05

1 stop24h 53m

$1,596

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 13/7

06:25-15:48

2 stops24h 23m

Chicago O'Hare Intl

Mon 10/8

18:45-07:05

1 stop21h 20m

$1,616

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 17/4

17:50-07:00

1 stop28h 10m

Chicago O'Hare Intl

Thu 23/4

21:14-11:50

2 stops47h 36m

$1,627

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/3

10:25-08:00

2 stops37h 35m

Chicago O'Hare Intl

Tue 21/4

08:50-07:20

1 stop31h 30m

$1,629

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/3

10:25-08:00

2 stops37h 35m

Chicago O'Hare Intl

Tue 21/4

07:13-07:20

3 stops33h 07m

$1,646

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-18:40

2 stops25h 00m

Chicago Midway

Tue 21/4

13:24-06:50

2 stops26h 26m

$1,713

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 2/5

09:15-22:28

2 stops28h 13m

Chicago Midway

Tue 16/6

14:00-06:50

2 stops25h 50m

$1,788

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 cheapest month to fly to Chicago?

If you don’t want to visit Chicago in April, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,211.

How far in advance should I book a flight 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 $1,681 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 $1,127 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 25% 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 February 2026, prices for Sydney to Chicago flights are approximately 2% 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	20h 18m
Direct flights	None

The fastest flight from Sydney to Chicago takes 20h 18m

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

Search flight deals

How far is Sydney Kingsford Smith to Chicago by plane?
There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 18m 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 February 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 (42% of total bookings). The next most popular airlines are Air Canada (21%), United Airlines (18%), and Air New Zealand (9%).

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
Qantas Airways	PriceFrom $978	Free cancellation	Rating 7.5 1,000 reviews	Search Qantas Airways flights
Air Canada	PriceFrom $1,065	Free cancellation	Rating 7.1 10,757 reviews	Search Air Canada flights
American Airlines	PriceFrom $1,096	Free cancellation	Rating 7.1 11,366 reviews	Search American Airlines flights
Air New Zealand	PriceFrom $1,330	Free cancellation	Rating 8.0 605 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,390	Free cancellation	Rating 7.4 9,363 reviews	Search United Airlines flights
ANA	PriceFrom $1,476	Free cancellation	Rating 8.4 1,103 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

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Chicago O'Hare Intl Airport

Cheap flights from Sydney to Chicago from $780

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 12/5. 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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Air New Zealand flights from Sydney to Chicago

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

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Our best Qantas Airways deals on Sydney to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Sydney to Chicago

What is the cheapest month to fly to Chicago?

How far in advance should I book a flight 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

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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According to popular flight searches on momondo this year

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