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Cheap flights from Sydney to Chicago from $540

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 19/5. 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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Cheap return flights

Enter your travel dates to find the best prices.
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
15:35 - 08:35
ORD
-
SYD
25h 00m
1 stop
$1,120Air Canada
Thu, 5 Mar - Wed, 18 Mar
Air Canada Logo
11:20 - 22:04
SYD
-
ORD
27h 44m
2 stops
Air Canada Logo
15:35 - 08:35
ORD
-
SYD
25h 00m
1 stop
$1,126Air Canada
Thu, 5 Mar - Wed, 18 Mar
Air Canada Logo
11:20 - 22:04
SYD
-
ORD
27h 44m
2 stops
Air Canada Logo
12:50 - 08:35
ORD
-
SYD
27h 45m
2 stops
$1,128Air Canada
Thu, 5 Mar - Wed, 18 Mar
Air Canada Logo
11:20 - 22:04
SYD
-
ORD
27h 44m
2 stops
Air Canada Logo
07:15 - 08:35
ORD
-
SYD
33h 20m
3 stops
$1,142Air Canada
Thu, 5 Mar - Wed, 18 Mar
Air Canada Logo
09:20 - 10:18
SYD
-
ORD
39h 58m
2 stops
Air Canada Logo
11:05 - 07:20
ORD
-
SYD
29h 15m
2 stops
$1,145Air Canada
Tue, 2 Jun - Tue, 4 Aug
Air Canada Logo
09:20 - 10:18
SYD
-
ORD
39h 58m
2 stops
Air Canada Logo
15:40 - 07:20
ORD
-
SYD
24h 40m
1 stop
$1,148Air Canada
Tue, 2 Jun - Tue, 4 Aug
Delta Logo
10:40 - 17:45
SYD
-
MDW
24h 05m
2 stops
Delta Logo
12:47 - 07:25
MDW
-
SYD
26h 38m
2 stops
$1,542Delta
Thu, 5 Mar - Wed, 18 Mar
Delta Logo
09:40 - 18:40
SYD
-
MDW
25h 00m
2 stops
Delta Logo
14:12 - 06:50
MDW
-
SYD
25h 38m
2 stops
$1,714Delta
Thu, 19 Mar - Tue, 21 Apr
Delta Logo
09:40 - 22:31
SYD
-
MDW
28h 51m
2 stops
Delta Logo
06:00 - 07:50
MDW
-
SYD
33h 50m
2 stops
$1,863Delta
Sat, 14 Mar - Sat, 28 Mar
Multiple Airlines Logo
14:00 - 21:12
SYD
-
MDW
24h 12m
2 stops
Multiple Airlines Logo
11:25 - 06:55
MDW
-
SYD
27h 30m
1 stop
$2,053Multiple Airlines
Thu, 5 Mar - Wed, 18 Mar

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
5 Mar
SYD11:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
18 Mar
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD08:35Sydney Kingsford Smith
$1,120
Air Canada
5 Mar
SYD11:20Sydney Kingsford Smith
27h 44m
2 stops
ORD22:04Chicago O'Hare Intl
18 Mar
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD08:35Sydney Kingsford Smith
$1,126
Air Canada
5 Mar
SYD11:20Sydney Kingsford Smith
27h 44m
2 stops
ORD22:04Chicago O'Hare Intl
18 Mar
ORD12:50Chicago O'Hare Intl
27h 45m
2 stops
SYD08:35Sydney Kingsford Smith
$1,128

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
13 Feb
SYD12:25Sydney Kingsford Smith
35h 55m
1 stop
ORD07:20Chicago O'Hare Intl
1 Mar
ORD18:20Chicago O'Hare Intl
32h 55m
2 stops
SYD20:15Sydney Kingsford Smith
$5,945
ANA
13 Feb
SYD12:25Sydney Kingsford Smith
35h 55m
1 stop
ORD07:20Chicago O'Hare Intl
1 Mar
ORD16:25Chicago O'Hare Intl
34h 50m
1 stop
SYD20:15Sydney Kingsford Smith
$7,046
ANA
13 Feb
SYD12:25Sydney Kingsford Smith
33h 36m
2 stops
ORD05:01Chicago O'Hare Intl
1 Mar
ORD18:20Chicago O'Hare Intl
32h 55m
2 stops
SYD20:15Sydney Kingsford Smith
$7,131

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 12 February 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

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/3

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 18/3

15:35-08:35

1 stop25h 00m

$1,120

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/3

11:20-22:04

2 stops27h 44m

Chicago O'Hare Intl

Wed 18/3

15:35-08:35

1 stop25h 00m

$1,126

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/3

11:20-22:04

2 stops27h 44m

Chicago O'Hare Intl

Wed 18/3

12:50-08:35

2 stops27h 45m

$1,128

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/3

11:20-22:04

2 stops27h 44m

Chicago O'Hare Intl

Wed 18/3

07:15-08:35

3 stops33h 20m

$1,142

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/6

09:20-10:18

2 stops39h 58m

Chicago O'Hare Intl

Tue 4/8

11:05-07:20

2 stops29h 15m

$1,145

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/6

09:20-10:18

2 stops39h 58m

Chicago O'Hare Intl

Tue 4/8

15:40-07:20

1 stop24h 40m

$1,148

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/3

10:40-17:45

2 stops24h 05m

Chicago Midway

Wed 18/3

12:47-07:25

2 stops26h 38m

$1,542

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-18:40

2 stops25h 00m

Chicago Midway

Tue 21/4

14:12-06:50

2 stops25h 38m

$1,714

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 14/3

09:40-22:31

2 stops28h 51m

Chicago Midway

Sat 28/3

06:00-07:50

2 stops33h 50m

$1,863

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/3

14:00-21:12

2 stops24h 12m

Chicago Midway

Wed 18/3

11:25-06:55

1 stop27h 30m

$2,053

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 cheapest month to fly to Chicago?

If you don’t want to visit Chicago in April, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,211.

How far in advance should I book a flight 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 $1,679 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 $1,127 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 63% 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 February 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 21m

Direct flights

None
The fastest flight from Sydney to Chicago takes 20h 21m
There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.
Search flight deals

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

    There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 21m 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
Qantas AirwaysPriceFrom $924Free cancellationRating
7.5
988 reviews
Search Qantas Airways flights
Air CanadaPriceFrom $1,065Free cancellationRating
7.1
10,710 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,096Free cancellationRating
7.2
11,272 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,330Free cancellationRating
8.0
582 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,389Free cancellationRating
7.4
9,282 reviews
Search United Airlines flights
ANAPriceFrom $1,476Free cancellationRating
8.4
1,091 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