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Cheap flights from New South Wales to Chicago from $638

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 15/10. 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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Find the cheapest flights from New South Wales to Chicago

Cheap return flights

Air Canada Logo
11:20 - 15:10SYD-ORD
44h 50m2 stops
Air Canada Logo
15:40 - 09:35ORD-SYD
24h 55m1 stop
$1,303Air Canada
Find Deal
Sat, 8 Nov - Sat, 22 Nov
Air Canada Logo
11:20 - 19:30SYD-ORD
25h 10m2 stops
Air Canada Logo
08:00 - 09:35ORD-SYD
32h 35m2 stops
$1,316Air Canada
Find Deal
Sat, 8 Nov - Sat, 22 Nov
Air Canada Logo
10:20 - 08:00SYD-ORD
37h 40m2 stops
Air Canada Logo
15:40 - 09:35ORD-SYD
24h 55m1 stop
$1,322Air Canada
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Qantas Airways Logo
09:10 - 15:51SYD-ORD
21h 41m1 stop
Qantas Airways Logo
18:03 - 09:00ORD-SYD
21h 57m1 stop
$1,421Qantas Airways
Find Deal
Tue, 30 Sep - Wed, 12 Nov
Logo
10:10 - 13:38SYD-MDW
43h 28m2 stops
Logo
05:10 - 08:05MDW-SYD
34h 55m2 stops
$1,432
Find Deal
Mon, 13 Oct - Mon, 20 Oct
Logo
11:20 - 12:37SYD-MDW
41h 17m2 stops
Logo
06:25 - 07:25MDW-SYD
32h 00m2 stops
$1,450
Find Deal
Thu, 30 Oct - Thu, 6 Nov
American Airlines Logo
09:10 - 17:18SYD-ORD
23h 08m2 stops
American Airlines Logo
15:00 - 09:00ORD-SYD
25h 00m1 stop
$1,481American Airlines
Find Deal
Tue, 30 Sep - Wed, 12 Nov
Delta Logo
09:25 - 18:35SYD-MDW
24h 10m2 stops
Delta Logo
13:14 - 08:30MDW-SYD
26h 16m2 stops
$1,507Delta
Find Deal
Tue, 30 Sep - Wed, 12 Nov
Delta Logo
09:25 - 19:00SYD-ORD
24h 35m2 stops
Delta Logo
13:38 - 08:30ORD-SYD
25h 52m2 stops
$1,507Delta
Find Deal
Tue, 30 Sep - Wed, 12 Nov
American Airlines Logo
09:10 - 21:22SYD-ORD
27h 12m1 stop
American Airlines Logo
12:15 - 06:10ORD-SYD
24h 55m1 stop
$1,580American Airlines
Find Deal
Sat, 4 Oct - Tue, 23 Dec

Air Canada flights from New South Wales to Chicago

Our best Air Canada deals on New South Wales to Chicago flight tickets
Air Canada
8 Nov
SYD11:20Sydney Kingsford Smith
44h 50m
2 stops
ORD15:10Chicago O'Hare Intl
22 Nov
ORD15:40Chicago O'Hare Intl
24h 55m
1 stop
SYD09:35Sydney Kingsford Smith
$1,303
Find similar
Air Canada
8 Nov
SYD11:20Sydney Kingsford Smith
25h 10m
2 stops
ORD19:30Chicago O'Hare Intl
22 Nov
ORD08:00Chicago O'Hare Intl
32h 35m
2 stops
SYD09:35Sydney Kingsford Smith
$1,316
Find similar
Air Canada
29 Oct
SYD10:20Sydney Kingsford Smith
37h 40m
2 stops
ORD08:00Chicago O'Hare Intl
5 Nov
ORD15:40Chicago O'Hare Intl
24h 55m
1 stop
SYD09:35Sydney Kingsford Smith
$1,322
Find similar

Cathay Pacific flights from New South Wales to Chicago

Our best Cathay Pacific deals on New South Wales to Chicago flight tickets
Cathay Pacific
19 Sept
SYD14:05Sydney Kingsford Smith
39h 20m
1 stop
ORD14:25Chicago O'Hare Intl
17 Oct
ORD16:00Chicago O'Hare Intl
27h 50m
1 stop
SYD11:50Sydney Kingsford Smith
$2,308
Find similar
Cathay Pacific
23 Sept
SYD10:10Sydney Kingsford Smith
43h 15m
1 stop
ORD14:25Chicago O'Hare Intl
28 Oct
ORD15:35Chicago O'Hare Intl
26h 00m
1 stop
SYD09:35Sydney Kingsford Smith
$7,693
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from New South Wales to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 78,305 searches. Data last updated 16 September 2025.
Use the filters below to find and compare flights from New South Wales to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

11:20-15:10

2 stops44h 50m

Chicago O'Hare Intl

Sat 22/11

15:40-09:35

1 stop24h 55m

$1,303

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

11:20-19:30

2 stops25h 10m

Chicago O'Hare Intl

Sat 22/11

08:00-09:35

2 stops32h 35m

$1,316

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 29/10

10:20-08:00

2 stops37h 40m

Chicago O'Hare Intl

Wed 5/11

15:40-09:35

1 stop24h 55m

$1,322

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:10-15:51

1 stop21h 41m

Chicago O'Hare Intl

Wed 12/11

18:03-09:00

1 stop21h 57m

$1,421

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 13/10

10:10-13:38

2 stops43h 28m

Chicago Midway

Mon 20/10

05:10-08:05

2 stops34h 55m

$1,432

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/10

11:20-12:37

2 stops41h 17m

Chicago Midway

Thu 6/11

06:25-07:25

2 stops32h 00m

$1,450

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:10-17:18

2 stops23h 08m

Chicago O'Hare Intl

Wed 12/11

15:00-09:00

1 stop25h 00m

$1,481

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Wed 12/11

13:14-08:30

2 stops26h 16m

$1,507

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:25-19:00

2 stops24h 35m

Chicago O'Hare Intl

Wed 12/11

13:38-08:30

2 stops25h 52m

$1,507

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 4/10

09:10-21:22

1 stop27h 12m

Chicago O'Hare Intl

Tue 23/12

12:15-06:10

1 stop24h 55m

$1,580

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in March, then you should wait until February to fly from New South Wales, when ticket prices are also cheap, with an average price of $1,117.

What is the cheapest day to depart on your flight to Chicago?

Our data shows that Tuesday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $1,685. Flights from New South Wales to Chicago on a Saturday will generally be more expensive and average around $1,984. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest New South Wales to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as $1,682. Flights in the morning are often more expensive, with an average ticket price of $1,861.

How far in advance should I book a flight 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 $1,477 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 $1,165 on momondo.

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

You could potentially save up to 34% 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

Direct flights

None
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

  • 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?

  • 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
Qantas AirwaysPriceFrom $988Free cancellationRating
7.5
905 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,170Free cancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $1,173Free cancellationRating
7.1
10,000 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,529Free cancellationRating
8.0
505 reviews
Search Air New Zealand flights
ANAPriceFrom $1,577Free cancellationRating
8.4
961 reviews
Search ANA flights
United AirlinesPriceFrom $1,628Free cancellationRating
7.4
8,929 reviews
Search United Airlines 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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport