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Cheap flights from New South Wales to Chicago from $632

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 15/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from New South Wales to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
06:00 - 07:30
ORD
-
SYD
34h 30m
1 stop
$1,444Multiple Airlines
Sat, 25 Apr - Sat, 9 May
Multiple Airlines Logo
14:00 - 04:49
SYD
-
ORD
30h 49m
2 stops
Multiple Airlines Logo
19:31 - 07:25
ORD
-
SYD
43h 54m
1 stop
$1,460Multiple Airlines
Tue, 17 Mar - Tue, 24 Mar
Air Canada Logo
10:25 - 08:00
SYD
-
ORD
37h 35m
2 stops
Air Canada Logo
15:40 - 07:20
ORD
-
SYD
24h 40m
1 stop
$1,526Air Canada
Thu, 19 Mar - Tue, 21 Apr
Air Canada Logo
10:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
10:35 - 08:35
ORD
-
SYD
30h 00m
2 stops
$1,533Air Canada
Tue, 17 Mar - Tue, 24 Mar
American Airlines Logo
11:20 - 17:46
SYD
-
ORD
22h 26m
1 stop
American Airlines Logo
16:30 - 07:05
ORD
-
SYD
23h 35m
1 stop
$1,537American Airlines
Thu, 19 Mar - Tue, 21 Apr
Air Canada Logo
10:20 - 11:18
SYD
-
ORD
40h 58m
2 stops
Air Canada Logo
12:50 - 08:35
ORD
-
SYD
27h 45m
2 stops
$1,540Air Canada
Tue, 17 Mar - Tue, 24 Mar
Air Canada Logo
10:25 - 20:10
SYD
-
ORD
25h 45m
2 stops
Air Canada Logo
07:13 - 07:20
ORD
-
SYD
33h 07m
3 stops
$1,543Air Canada
Thu, 19 Mar - Tue, 21 Apr
Delta Logo
09:40 - 18:40
SYD
-
MDW
25h 00m
2 stops
Delta Logo
13:23 - 06:50
MDW
-
SYD
26h 27m
2 stops
$1,725Delta
Thu, 19 Mar - Tue, 21 Apr
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
12:53 - 06:50
MDW
-
SYD
26h 57m
2 stops
$1,731Delta
Thu, 19 Mar - Tue, 21 Apr
Air New Zealand Logo
10:55 - 20:23
OOL
-
ORD
24h 28m
2 stops
Air New Zealand Logo
14:35 - 06:45
ORD
-
OOL
25h 10m
2 stops
$1,754Air New Zealand
Tue, 17 Mar - Tue, 24 Mar

Air Canada flights from New South Wales to Chicago

Our best Air Canada deals on New South Wales to Chicago flight tickets
Air Canada
19 Mar
SYD10:25Sydney Kingsford Smith
37h 35m
2 stops
ORD08:00Chicago O'Hare Intl
21 Apr
ORD15:40Chicago O'Hare Intl
24h 40m
1 stop
SYD07:20Sydney Kingsford Smith
$1,526
Air Canada
17 Mar
SYD10:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
24 Mar
ORD10:35Chicago O'Hare Intl
30h 00m
2 stops
SYD08:35Sydney Kingsford Smith
$1,533
Air Canada
17 Mar
SYD10:20Sydney Kingsford Smith
40h 58m
2 stops
ORD11:18Chicago O'Hare Intl
24 Mar
ORD12:50Chicago O'Hare Intl
27h 45m
2 stops
SYD08:35Sydney Kingsford Smith
$1,540

American Airlines flights from New South Wales to Chicago

Our best American Airlines deals on New South Wales to Chicago flight tickets
American Airlines
19 Mar
SYD11:20Sydney Kingsford Smith
22h 26m
1 stop
ORD17:46Chicago O'Hare Intl
21 Apr
ORD16:30Chicago O'Hare Intl
23h 35m
1 stop
SYD07:05Sydney Kingsford Smith
$1,537
American Airlines
25 Feb
SYD14:05Sydney Kingsford Smith
24h 20m
1 stop
ORD21:25Chicago O'Hare Intl
2 Mar
ORD09:29Chicago O'Hare Intl
28h 26m
1 stop
SYD06:55Sydney Kingsford Smith
$1,587
American Airlines
22 Feb
SYD11:20Sydney Kingsford Smith
23h 25m
2 stops
ORD17:45Chicago O'Hare Intl
9 Mar
ORD16:49Chicago O'Hare Intl
24h 11m
2 stops
SYD09:00Sydney Kingsford Smith
$1,612

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 2 February 2026.
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 25/4

13:15-05:50

2 stops31h 35m

Chicago O'Hare Intl

Sat 9/5

06:00-07:30

1 stop34h 30m

$1,444

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 17/3

14:00-04:49

2 stops30h 49m

Chicago O'Hare Intl

Tue 24/3

19:31-07:25

1 stop43h 54m

$1,460

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/3

10:25-08:00

2 stops37h 35m

Chicago O'Hare Intl

Tue 21/4

15:40-07:20

1 stop24h 40m

$1,526

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 17/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 24/3

10:35-08:35

2 stops30h 00m

$1,533

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/3

11:20-17:46

1 stop22h 26m

Chicago O'Hare Intl

Tue 21/4

16:30-07:05

1 stop23h 35m

$1,537

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 17/3

10:20-11:18

2 stops40h 58m

Chicago O'Hare Intl

Tue 24/3

12:50-08:35

2 stops27h 45m

$1,540

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/3

10:25-20:10

2 stops25h 45m

Chicago O'Hare Intl

Tue 21/4

07:13-07:20

3 stops33h 07m

$1,543

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-18:40

2 stops25h 00m

Chicago Midway

Tue 21/4

13:23-06:50

2 stops26h 27m

$1,725

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Tue 21/4

12:53-06:50

2 stops26h 57m

$1,731

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Tue 17/3

10:55-20:23

2 stops24h 28m

Chicago O'Hare Intl

Tue 24/3

14:35-06:45

2 stops25h 10m

$1,754

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 May to fly from New South Wales, when ticket prices are also cheap, with an average price of $1,084.

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 $1,377 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 $1,137 on momondo.

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

You could potentially save up to 65% 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

19h 31m

Direct flights

None
The fastest flight from New South Wales to Chicago takes 19h 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

  • 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 $940Free cancellationRating
7.5
985 reviews
Search Qantas Airways flights
Air CanadaPriceFrom $1,088Free cancellationRating
7.1
10,676 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,119Free cancellationRating
7.2
11,213 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,358Free cancellationRating
8.0
578 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,419Free cancellationRating
7.4
9,232 reviews
Search United Airlines flights
ANAPriceFrom $1,508Free cancellationRating
8.4
1,082 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.

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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