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 New South Wales 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 New South Wales to Chicago?

Delta is the most popular carrier operating from New South Wales to Chicago

When did momondo last update prices for flights from New South Wales to Chicago?

Prices for flights from New South Wales to Chicago are updated daily.

How many operators does momondo search for flights from New South Wales to Chicago?

As of May 2026, there are 6 operators available to choose from for flights from New South Wales to Chicago.

How old do you have to be to fly from New South Wales to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from New South Wales to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$921 Cheap Flights from New South Wales to Chicago in 2026

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Find the cheapest flights from New South Wales to Chicago

Round-trip

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

17:50 - 06:39

SYD

ORD

27h 49m

1 stop

07:40 - 07:30

ORD

SYD

32h 50m

2 stops

$1,673Multiple Airlines

Mon, 18 May - Tue, 2 Jun

17:50 - 06:39

SYD

ORD

27h 49m

1 stop

07:40 - 07:30

ORD

SYD

32h 50m

2 stops

$1,817Multiple Airlines

Tue, 19 May - Wed, 3 Jun

17:50 - 06:17

SYD

ORD

27h 27m

1 stop

09:28 - 07:30

ORD

SYD

31h 02m

2 stops

$1,826Multiple Airlines

Mon, 20 Jul - Mon, 10 Aug

17:50 - 06:39

SYD

ORD

27h 49m

1 stop

06:00 - 07:30

ORD

SYD

34h 30m

2 stops

$1,835Multiple Airlines

Tue, 19 May - Wed, 3 Jun

17:50 - 06:17

SYD

ORD

27h 27m

1 stop

09:28 - 11:50

ORD

SYD

35h 22m

2 stops

$1,851Multiple Airlines

Mon, 20 Jul - Thu, 13 Aug

09:15 - 18:33

SYD

MDW

24h 18m

2 stops

13:00 - 06:50

MDW

SYD

26h 50m

2 stops

$2,351Delta

Thu, 4 Jun - Wed, 12 Aug

09:15 - 17:56

SYD

MDW

23h 41m

2 stops

14:00 - 06:50

MDW

SYD

25h 50m

2 stops

$2,357Delta

Thu, 4 Jun - Wed, 12 Aug

09:20 - 13:55

OOL

ORD

43h 35m

2 stops

16:00 - 15:05

ORD

OOL

32h 05m

2 stops

$2,955Cathay Pacific

Fri, 22 May - Sat, 15 Aug

06:00 - 14:35

OOL

ORD

23h 35m

2 stops

18:20 - 12:25

ORD

OOL

27h 05m

2 stops

$2,963United Airlines

Sat, 13 Jun - Sat, 20 Jun

11:55 - 04:51

OOL

ORD

31h 56m

2 stops

16:45 - 10:45

ORD

OOL

27h 00m

2 stops

$3,214Air New Zealand

Sat, 27 Jun - Wed, 1 Jul

Air Canada flights from New South Wales to Chicago

Our best Air Canada deals on New South Wales to Chicago flight tickets

Air Canada

12 May

SYD09:20Sydney Kingsford Smith

22h 15m

2 stops

ORD16:35Chicago O'Hare Intl

17 May

ORD18:21Chicago O'Hare Intl

45h 59m

2 stops

SYD07:20Sydney Kingsford Smith

$2,533

Air Canada

12 May

SYD09:20Sydney Kingsford Smith

22h 15m

2 stops

ORD16:35Chicago O'Hare Intl

17 May

ORD15:40Chicago O'Hare Intl

24h 40m

1 stop

SYD07:20Sydney Kingsford Smith

$2,641

Air Canada

9 May

SYD09:20Sydney Kingsford Smith

20h 25m

1 stop

ORD14:45Chicago O'Hare Intl

13 May

ORD08:45Chicago O'Hare Intl

31h 35m

2 stops

SYD07:20Sydney Kingsford Smith

$2,799

ANA flights from New South Wales to Chicago

Our best ANA deals on New South Wales to Chicago flight tickets

ANA

10 Sept

SYD11:45Sydney Kingsford Smith

32h 00m

2 stops

ORD04:45Chicago O'Hare Intl

22 Sept

ORD17:45Chicago O'Hare Intl

24h 40m

1 stop

SYD09:25Sydney Kingsford Smith

$1,926

ANA

18 July

SYD11:45Sydney Kingsford Smith

32h 06m

2 stops

ORD04:51Chicago O'Hare Intl

26 July

ORD17:45Chicago O'Hare Intl

34h 25m

1 stop

SYD19:10Sydney Kingsford Smith

$1,996

ANA

5 June

SYD11:45Sydney Kingsford Smith

47h 50m

2 stops

ORD20:35Chicago O'Hare Intl

12 Aug

ORD17:45Chicago O'Hare Intl

34h 25m

1 stop

SYD19:10Sydney Kingsford Smith

$1,999

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 18/5

17:50-06:39

1 stop27h 49m

Chicago O'Hare Intl

Tue 2/6

07:40-07:30

2 stops32h 50m

$1,673

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 19/5

17:50-06:39

1 stop27h 49m

Chicago O'Hare Intl

Wed 3/6

07:40-07:30

2 stops32h 50m

$1,817

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 20/7

17:50-06:17

1 stop27h 27m

Chicago O'Hare Intl

Mon 10/8

09:28-07:30

2 stops31h 02m

$1,826

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 19/5

17:50-06:39

1 stop27h 49m

Chicago O'Hare Intl

Wed 3/6

06:00-07:30

2 stops34h 30m

$1,835

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 20/7

17:50-06:17

1 stop27h 27m

Chicago O'Hare Intl

Thu 13/8

09:28-11:50

2 stops35h 22m

$1,851

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/6

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 12/8

13:00-06:50

2 stops26h 50m

$2,351

Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/6

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 12/8

14:00-06:50

2 stops25h 50m

$2,357

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Fri 22/5

09:20-13:55

2 stops43h 35m

Chicago O'Hare Intl

Sat 15/8

16:00-15:05

2 stops32h 05m

$2,955

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Sat 13/6

06:00-14:35

2 stops23h 35m

Chicago O'Hare Intl

Sat 20/6

18:20-12:25

2 stops27h 05m

$2,963

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Sat 27/6

11:55-04:51

2 stops31h 56m

Chicago O'Hare Intl

Wed 1/7

16:45-10:45

2 stops27h 00m

$3,214

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 New South Wales 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

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 New South Wales, when ticket prices are also cheap, with an average price of $870.

How far in advance should I book a flight from New South Wales to Chicago?

You are more likely to see cheaper flights to Chicago from New South Wales when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,855 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 New South Wales for as low as $1,369 on momondo.

Can stopping save me money on New South Wales to Chicago flights?

You could potentially save up to 52% on your flight if you consider stops on a New South Wales to Chicago flight.

Cheap New South Wales to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New South Wales to Chicago

Fastest flight time	22h 31m
Direct flights	None

The fastest flight from New South Wales to Chicago takes 22h 31m

There are no direct flights from New South Wales to Chicago. There are no popular flight routes from New South Wales to Chicago.

Search flight deals

Frequently asked questions about flying from New South Wales to Chicago

When did momondo last update prices for flights from New South Wales to Chicago?
Prices for flights from New South Wales to Chicago are updated daily.
How many operators does momondo search for flights from New South Wales to Chicago?
As of May 2026, there are 6 operators available to choose from for flights from New South Wales to Chicago.
How old do you have to be to fly from New South Wales to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from New South Wales to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from New South Wales to Chicago

Compare and see reviews for airlines that fly from New South Wales to Chicago with momondo

Airline	Rating	Free cancellation	Price
Air Canada	PriceFrom $1,051	Free cancellation	Rating 7.1 10,993 reviews	Search Air Canada flights
American Airlines	PriceFrom $1,082	Free cancellation	Rating 7.1 11,672 reviews	Search American Airlines flights
Qantas Airways	PriceFrom $1,224	Free cancellation	Rating 7.5 1,030 reviews	Search Qantas Airways flights
Air New Zealand	PriceFrom $1,313	Free cancellation	Rating 8.0 639 reviews	Search Air New Zealand flights
United Airlines	PriceFrom $1,372	Free cancellation	Rating 7.4 9,680 reviews	Search United Airlines flights
ANA	PriceFrom $1,457	Free cancellation	Rating 8.3 1,205 reviews	Search ANA flights

Why use momondo?

Why should I use momondo to find a flight deal from New South Wales to Chicago?

It is quick and easy to find New South Wales to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from New South Wales to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from New South Wales on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from New South Wales to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from New South Wales.

I’m not ready to book a flight from New South Wales to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from New South Wales are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

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Cheap flights from New South Wales to Chicago from $921

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New South Wales to Chicago departing on 9/10. 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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Big names, great deals

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Filter for what you want

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Air Canada flights from New South Wales to Chicago

Our best Air Canada deals on New South Wales to Chicago flight tickets

ANA flights from New South Wales to Chicago

Our best ANA deals on New South Wales to Chicago flight tickets

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How to get the cheapest flight ticket from New South Wales to Chicago

What is the cheapest month to fly to Chicago?

How far in advance should I book a flight from New South Wales to Chicago?

Can stopping save me money on New South Wales to Chicago flights?

What is the cheapest airline that flies from New South Wales to Chicago?

Which airlines fly to Chicago?

Cheap New South Wales to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New South Wales to Chicago

Fastest flight time

Direct flights

Frequently asked questions about flying from New South Wales to Chicago

Best airlines flying from New South Wales to Chicago

Compare and see reviews for airlines that fly from New South Wales 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

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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