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Cheap flights from Sydney to Chicago from $694

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 8/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Sydney to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
13:15 - 09:20SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 05m3 stops Nadi Los Angeles Los Angeles Atlanta Hartsfield-Jackson
Multiple Airlines Logo
06:00 - 11:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
38h 50m3 stops Dallas/Fort Worth Los Angeles Los Angeles Nadi
$1,144Multiple Airlines
Wed, 9 Sep - Wed, 16 Sep
Multiple Airlines Logo
13:15 - 06:17SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
32h 02m2 stops Nadi Los Angeles Los Angeles
Multiple Airlines Logo
06:30 - 22:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
48h 55m3 stops Denver Intl Los Angeles Los Angeles Nadi
$1,168Multiple Airlines
Tue, 8 Sep - Tue, 22 Sep
Air New Zealand Logo
09:55 - 21:46SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 51m2 stops Auckland Intl Los Angeles Los Angeles
Air New Zealand Logo
14:10 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 25m2 stops Los Angeles Los Angeles Auckland Intl
$1,837Air New Zealand
Wed, 2 Dec - Mon, 8 Feb
Air New Zealand Logo
09:55 - 23:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 10m2 stops Auckland Intl Los Angeles Los Angeles
Air New Zealand Logo
16:00 - 10:40ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
27h 40m2 stops San Francisco Auckland Intl
$1,839Air New Zealand
Tue, 8 Sep - Tue, 22 Sep
American Airlines Logo
11:20 - 06:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 45m1 stop Los Angeles Los Angeles
American Airlines Logo
08:05 - 06:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 20m1 stop San Francisco
$2,053American Airlines
Wed, 11 Nov - Sun, 15 Nov
American Airlines Logo
11:20 - 06:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 45m1 stop Los Angeles Los Angeles
American Airlines Logo
08:05 - 06:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 20m1 stop San Francisco
$2,059American Airlines
Wed, 11 Nov - Sun, 15 Nov
Qantas Airways Logo
09:10 - 14:54SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 44m1 stop Los Angeles Los Angeles
Qantas Airways Logo
19:03 - 07:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 27m1 stop Los Angeles Los Angeles
$2,122Qantas Airways
Mon, 7 Sep - Tue, 22 Sep
Qantas Airways Logo
11:15 - 17:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 44m1 stop Los Angeles Los Angeles
Qantas Airways Logo
12:00 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
28h 00m1 stop Los Angeles Los Angeles
$2,170Qantas Airways
Thu, 3 Dec - Mon, 8 Feb
Air Canada Logo
11:20 - 14:37SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 17m1 stop Vancouver Intl
Air Canada Logo
15:35 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 00m1 stop Vancouver Intl
$2,229Air Canada
Thu, 3 Dec - Thu, 11 Feb
Air Canada Logo
11:20 - 14:37SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 17m1 stop Vancouver Intl
Air Canada Logo
13:55 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$2,232Air Canada
Wed, 2 Dec - Wed, 10 Feb

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Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets
Air New Zealand
2 Dec
SYD09:55Sydney Kingsford Smith
28h 51m
2 stops
ORD21:46Chicago O'Hare Intl
8 Feb
ORD14:10Chicago O'Hare Intl
25h 25m
2 stops
SYD08:35Sydney Kingsford Smith
$1,837
Air New Zealand
8 Sept
SYD09:55Sydney Kingsford Smith
28h 10m
2 stops
ORD23:05Chicago O'Hare Intl
22 Sept
ORD16:00Chicago O'Hare Intl
27h 40m
2 stops
SYD10:40Sydney Kingsford Smith
$1,838
Air New Zealand
9 Sept
SYD09:55Sydney Kingsford Smith
28h 10m
2 stops
ORD23:05Chicago O'Hare Intl
15 Sept
ORD16:00Chicago O'Hare Intl
25h 45m
2 stops
SYD08:45Sydney Kingsford Smith
$1,840

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets
American Airlines
11 Nov
SYD11:20Sydney Kingsford Smith
35h 45m
1 stop
ORD06:05Chicago O'Hare Intl
15 Nov
ORD08:05Chicago O'Hare Intl
29h 20m
1 stop
SYD06:25Sydney Kingsford Smith
$2,059
American Airlines
28 Sept
SYD09:10Sydney Kingsford Smith
21h 43m
1 stop
ORD15:53Chicago O'Hare Intl
5 Oct
ORD18:55Chicago O'Hare Intl
21h 10m
1 stop
SYD08:05Sydney Kingsford Smith
$2,179
American Airlines
28 Aug
SYD09:10Sydney Kingsford Smith
42h 13m
1 stop
ORD12:23Chicago O'Hare Intl
1 Sept
ORD15:20Chicago O'Hare Intl
24h 05m
1 stop
SYD06:25Sydney Kingsford Smith
$2,540

momondo Fare Finder

 
Customise your flight search to find flights from Sydney 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 15 August 2026.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 9/9

13:15-09:20

3 stops35h 05m

Chicago O'Hare Intl

Wed 16/9

06:00-11:50

3 stops38h 50m

$1,144

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Tue 22/9

06:30-22:25

3 stops48h 55m

$1,168

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 2/12

09:55-21:46

2 stops28h 51m

Chicago O'Hare Intl

Mon 8/2

14:10-08:35

2 stops25h 25m

$1,837

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:55-23:05

2 stops28h 10m

Chicago O'Hare Intl

Tue 22/9

16:00-10:40

2 stops27h 40m

$1,838

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 11/11

11:20-06:05

1 stop35h 45m

Chicago O'Hare Intl

Sun 15/11

08:05-06:25

1 stop29h 20m

$2,053

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 11/11

11:20-06:05

1 stop35h 45m

Chicago O'Hare Intl

Sun 15/11

08:05-06:25

1 stop29h 20m

$2,059
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 7/9

09:10-14:54

1 stop20h 44m

Chicago O'Hare Intl

Tue 22/9

19:03-07:30

1 stop21h 27m

$2,122

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/12

11:15-17:59

1 stop23h 44m

Chicago O'Hare Intl

Mon 8/2

12:00-09:00

1 stop28h 00m

$2,170

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/12

11:20-14:37

1 stop20h 17m

Chicago O'Hare Intl

Thu 11/2

15:35-09:35

1 stop25h 00m

$2,229

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 2/12

11:20-14:37

1 stop20h 17m

Chicago O'Hare Intl

Wed 10/2

13:55-09:35

2 stops26h 40m

$2,232

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 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

What is the typical price of a round-trip flight between Sydney and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $1,363 to $1,891.
The lowest price recently found on this route was $1,144.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in September, then you should wait until October to fly from Sydney, when ticket prices are also cheap, with an average price of $1,482.

How far in advance should I book a flight from Sydney 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 $1,937 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 $1,235 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 17% 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 August 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 10m

Direct flights

None
The fastest flight from Sydney to Chicago takes 20h 10m
There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.
Search flight deals

Frequently asked questions about flying from Sydney to Chicago

  • How far is Sydney Kingsford Smith to Chicago by plane?

    There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 10m 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?

  • 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?

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
Air CanadaPriceFrom $1,069Free cancellationRating
7.1
11,479 reviews
Search Air Canada flights
Qantas AirwaysPriceFrom $1,245Free cancellationRating
7.5
1,083 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,246Free cancellationRating
7.1
11,948 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,335Free cancellationRating
8.0
662 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,395Free cancellationRating
7.4
10,105 reviews
Search United Airlines 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

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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