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Cheap flights from New South Wales to Chicago from $849

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 15/12. 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
10:20 - 16:42SYD-ORD
22h 22m1 stop
Air Canada Logo
13:10 - 09:35ORD-SYD
27h 25m1 stop
$1,326Air Canada
Find Deal
Thu, 16 Oct - Sun, 9 Nov
Air Canada Logo
10:20 - 09:51SYD-ORD
39h 31m2 stops
Air Canada Logo
20:15 - 09:35ORD-SYD
44h 20m2 stops
$1,331Air Canada
Find Deal
Wed, 15 Oct - Sat, 8 Nov
Air Canada Logo
07:00 - 16:42SYD-ORD
25h 42m2 stops
Air Canada Logo
13:10 - 09:35ORD-SYD
27h 25m1 stop
$1,347Air Canada
Find Deal
Wed, 15 Oct - Sun, 9 Nov
Logo
08:15 - 09:09OOL-ORD
63h 54m3 stops
Logo
15:40 - 15:10ORD-OOL
32h 30m2 stops
$1,417
Find Deal
Thu, 23 Oct - Thu, 30 Oct
Logo
13:00 - 09:09OOL-ORD
59h 09m3 stops
Logo
14:00 - 18:00ORD-OOL
37h 00m3 stops
$1,428
Find Deal
Thu, 23 Oct - Thu, 30 Oct
Delta Logo
10:25 - 18:25SYD-MDW
24h 00m2 stops
Delta Logo
10:35 - 07:35MDW-SYD
29h 00m2 stops
$1,506Delta
Find Deal
Thu, 9 Oct - Wed, 22 Oct
Delta Logo
09:25 - 17:35SYD-MDW
23h 10m2 stops
Delta Logo
12:47 - 08:30MDW-SYD
26h 43m2 stops
$1,511Delta
Find Deal
Tue, 30 Sep - Wed, 12 Nov
United Airlines Logo
11:20 - 18:25SYD-ORD
23h 05m2 stops
United Airlines Logo
21:08 - 07:00ORD-SYD
41h 52m1 stop
$1,585United Airlines
Find Deal
Sat, 25 Oct - Sat, 1 Nov
Air New Zealand Logo
10:55 - 23:15OOL-ORD
27h 20m2 stops
Air New Zealand Logo
15:40 - 09:45ORD-OOL
27h 05m2 stops
$1,615Air New Zealand
Find Deal
Thu, 23 Oct - Thu, 30 Oct
United Airlines Logo
11:20 - 19:35SYD-ORD
24h 15m2 stops
United Airlines Logo
18:15 - 09:05ORD-SYD
22h 50m2 stops
$1,750United Airlines
Find Deal
Thu, 23 Oct - Thu, 30 Oct

American Airlines flights from New South Wales to Chicago

Our best American Airlines deals on New South Wales to Chicago flight tickets
American Airlines
29 Sept
SYD09:10Sydney Kingsford Smith
19h 34m
1 stop
ORD13:44Chicago O'Hare Intl
18 Dec
ORD15:13Chicago O'Hare Intl
23h 12m
1 stop
SYD07:25Sydney Kingsford Smith
$1,729
Find similar
American Airlines
18 Sept
SYD09:10Sydney Kingsford Smith
22h 37m
1 stop
ORD16:47Chicago O'Hare Intl
17 Oct
ORD07:00Chicago O'Hare Intl
33h 05m
1 stop
SYD08:05Sydney Kingsford Smith
$1,731
Find similar
American Airlines
3 Dec
SYD11:15Sydney Kingsford Smith
21h 47m
1 stop
ORD16:02Chicago O'Hare Intl
23 Dec
ORD15:13Chicago O'Hare Intl
24h 47m
1 stop
SYD09:00Sydney Kingsford Smith
$1,738
Find similar

United Airlines flights from New South Wales to Chicago

Our best United Airlines deals on New South Wales to Chicago flight tickets
United Airlines
25 Oct
SYD11:20Sydney Kingsford Smith
23h 05m
2 stops
ORD18:25Chicago O'Hare Intl
1 Nov
ORD21:08Chicago O'Hare Intl
41h 52m
1 stop
SYD07:00Sydney Kingsford Smith
$1,585
Find similar
United Airlines
12 Sept
SYD09:30Sydney Kingsford Smith
23h 56m
2 stops
ORD18:26Chicago O'Hare Intl
26 Sept
ORD21:13Chicago O'Hare Intl
42h 42m
1 stop
SYD06:55Sydney Kingsford Smith
$1,632
Find similar
United Airlines
12 Sept
SYD10:20Sydney Kingsford Smith
19h 43m
1 stop
ORD15:03Chicago O'Hare Intl
26 Sept
ORD21:13Chicago O'Hare Intl
42h 42m
1 stop
SYD06:55Sydney Kingsford Smith
$1,638
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 10 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

Thu 16/10

10:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Sun 9/11

13:10-09:35

1 stop27h 25m

$1,326

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 15/10

10:20-09:51

2 stops39h 31m

Chicago O'Hare Intl

Sat 8/11

20:15-09:35

2 stops44h 20m

$1,331

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 15/10

07:00-16:42

2 stops25h 42m

Chicago O'Hare Intl

Sun 9/11

13:10-09:35

1 stop27h 25m

$1,347

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Thu 23/10

08:15-09:09

3 stops63h 54m

Chicago O'Hare Intl

Thu 30/10

15:40-15:10

2 stops32h 30m

$1,417

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Thu 23/10

13:00-09:09

3 stops59h 09m

Chicago O'Hare Intl

Thu 30/10

14:00-18:00

3 stops37h 00m

$1,428

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 9/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Wed 22/10

10:35-07:35

2 stops29h 00m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Wed 12/11

12:47-08:30

2 stops26h 43m

$1,511

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 25/10

11:20-18:25

2 stops23h 05m

Chicago O'Hare Intl

Sat 1/11

21:08-07:00

1 stop41h 52m

$1,585

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Thu 23/10

10:55-23:15

2 stops27h 20m

Chicago O'Hare Intl

Thu 30/10

15:40-09:45

2 stops27h 05m

$1,615

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/10

11:20-19:35

2 stops24h 15m

Chicago O'Hare Intl

Thu 30/10

18:15-09:05

2 stops22h 50m

$1,750

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 February, then you should wait until March to fly from New South Wales, when ticket prices are also cheap, with an average price of $1,129.

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 $1,701. Flights from New South Wales to Chicago on a Saturday will generally be more expensive and average around $2,003. 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 $1,698. Flights in the morning are often more expensive, with an average ticket price of $1,879.

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 $1,546 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 $1,176 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 $998Free cancellationRating
7.5
905 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,182Free cancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $1,250Free cancellationRating
7.1
10,000 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,544Free cancellationRating
8.0
506 reviews
Search Air New Zealand flights
ANAPriceFrom $1,592Free cancellationRating
8.4
962 reviews
Search ANA flights
United AirlinesPriceFrom $1,644Free cancellationRating
7.4
8,937 reviews
Search United Airlines flights
Virgin AustraliaPriceFrom $1,746Free cancellationRating
7.5
416 reviews
Search Virgin Australia 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