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Cheap flights from Sydney to Chicago from $893

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 10/11. 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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Cheap return flights

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American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,422American Airlines
Thu, 29 Oct - Sun, 1 Nov
American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,424American Airlines
Thu, 29 Oct - Sun, 1 Nov
American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,426American Airlines
Thu, 29 Oct - Sun, 1 Nov
American Airlines Logo
11:15 - 12:11
SYD
-
ORD
40h 56m
1 stop
American Airlines Logo
08:35 - 06:10
ORD
-
SYD
28h 35m
1 stop
$1,429American Airlines
Thu, 29 Oct - Sun, 1 Nov
American Airlines Logo
11:15 - 16:52
SYD
-
ORD
22h 37m
1 stop
American Airlines Logo
07:00 - 09:00
ORD
-
SYD
33h 00m
1 stop
$1,430American Airlines
Mon, 2 Nov - Mon, 9 Nov
Delta Logo
10:40 - 16:49
SYD
-
ORD
23h 09m
2 stops
Delta Logo
15:50 - 08:30
ORD
-
SYD
23h 40m
2 stops
$1,455Delta
Mon, 2 Nov - Tue, 10 Nov
American Airlines Logo
11:15 - 16:55
SYD
-
ORD
21h 40m
1 stop
American Airlines Logo
15:00 - 09:00
ORD
-
SYD
25h 00m
1 stop
$1,500American Airlines
Sun, 1 Nov - Wed, 11 Nov
American Airlines Logo
11:15 - 16:52
SYD
-
ORD
22h 37m
1 stop
American Airlines Logo
13:49 - 06:25
ORD
-
SYD
23h 36m
1 stop
$1,511American Airlines
Thu, 5 Nov - Thu, 12 Nov
American Airlines Logo
09:10 - 18:05
SYD
-
ORD
23h 55m
1 stop
American Airlines Logo
20:55 - 06:55
ORD
-
SYD
42h 00m
1 stop
$1,514American Airlines
Thu, 1 Oct - Fri, 9 Oct
Delta Logo
10:40 - 20:34
SYD
-
ORD
25h 54m
2 stops
Delta Logo
18:30 - 08:30
ORD
-
SYD
21h 00m
1 stop
$1,527Delta
Sun, 1 Nov - Tue, 10 Nov

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets
American Airlines
29 Oct
SYD11:15Sydney Kingsford Smith
34h 46m
1 stop
ORD06:01Chicago O'Hare Intl
1 Nov
ORD10:15Chicago O'Hare Intl
26h 55m
1 stop
SYD06:10Sydney Kingsford Smith
$1,422
American Airlines
29 Oct
SYD11:15Sydney Kingsford Smith
34h 46m
1 stop
ORD06:01Chicago O'Hare Intl
1 Nov
ORD10:15Chicago O'Hare Intl
26h 55m
1 stop
SYD06:10Sydney Kingsford Smith
$1,424
American Airlines
29 Oct
SYD11:15Sydney Kingsford Smith
34h 46m
1 stop
ORD06:01Chicago O'Hare Intl
1 Nov
ORD10:15Chicago O'Hare Intl
26h 55m
1 stop
SYD06:10Sydney Kingsford Smith
$1,426

Delta flights from Sydney to Chicago

Our best Delta deals on Sydney to Chicago flight tickets
Delta
2 Nov
SYD10:40Sydney Kingsford Smith
23h 09m
2 stops
ORD16:49Chicago O'Hare Intl
10 Nov
ORD15:50Chicago O'Hare Intl
23h 40m
2 stops
SYD08:30Sydney Kingsford Smith
$1,455
Delta
1 Nov
SYD10:40Sydney Kingsford Smith
25h 54m
2 stops
ORD20:34Chicago O'Hare Intl
11 Nov
ORD18:30Chicago O'Hare Intl
21h 00m
1 stop
SYD08:30Sydney Kingsford Smith
$1,527
Delta
17 July
SYD09:15Sydney Kingsford Smith
27h 14m
2 stops
ORD21:29Chicago O'Hare Intl
30 Sept
ORD14:05Chicago O'Hare Intl
25h 45m
2 stops
SYD06:50Sydney Kingsford Smith
$1,986

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 4 June 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 - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Sun 1/11

10:15-06:10

1 stop26h 55m

$1,422

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Sun 1/11

10:15-06:10

1 stop26h 55m

$1,424

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Sun 1/11

10:15-06:10

1 stop26h 55m

$1,426

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/10

11:15-12:11

1 stop40h 56m

Chicago O'Hare Intl

Sun 1/11

08:35-06:10

1 stop28h 35m

$1,429

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/11

11:15-16:52

1 stop22h 37m

Chicago O'Hare Intl

Mon 9/11

07:00-09:00

1 stop33h 00m

$1,430

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/11

10:40-16:49

2 stops23h 09m

Chicago O'Hare Intl

Tue 10/11

15:50-08:30

2 stops23h 40m

$1,455

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 1/11

11:15-16:55

1 stop21h 40m

Chicago O'Hare Intl

Wed 11/11

15:00-09:00

1 stop25h 00m

$1,500
Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/11

11:15-16:52

1 stop22h 37m

Chicago O'Hare Intl

Thu 12/11

13:49-06:25

1 stop23h 36m

$1,511

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:10-18:05

1 stop23h 55m

Chicago O'Hare Intl

Fri 9/10

20:55-06:55

1 stop42h 00m

$1,514

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 1/11

10:40-20:34

2 stops25h 54m

Chicago O'Hare Intl

Tue 10/11

18:30-08:30

1 stop21h 00m

$1,527

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 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?

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 Sydney, when ticket prices are also cheap, with an average price of $876.

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 $1,848 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 $1,380 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 2% 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 June 2026, prices for Sydney to Chicago flights are approximately 4% more expensive 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

19h 31m

Direct flights

None
The fastest flight from Sydney to Chicago takes 19h 31m
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. 19h 31m 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 $1,059Free cancellationRating
7.1
11,126 reviews
Search Air Canada flights
Qantas AirwaysPriceFrom $1,234Free cancellationRating
7.5
1,042 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,235Free cancellationRating
7.1
11,640 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,323Free cancellationRating
8.0
645 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,382Free cancellationRating
7.4
9,774 reviews
Search United Airlines flights
ANAPriceFrom $1,494Free cancellationRating
8.3
1,220 reviews
Search ANA 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.

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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