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Cheap flights from Sydney to Chicago from $719

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 4/5. 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 New Zealand Logo
13:55 - 22:59
SYD
-
ORD
26h 04m
2 stops
Air New Zealand Logo
16:00 - 08:45
ORD
-
SYD
24h 45m
2 stops
$1,435Air New Zealand
Mon, 2 Mar - Mon, 9 Mar
Air Canada Logo
11:20 - 22:05
SYD
-
ORD
27h 45m
2 stops
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,483Air Canada
Mon, 2 Feb - Mon, 16 Feb
Air Canada Logo
11:20 - 22:05
SYD
-
ORD
27h 45m
2 stops
Air Canada Logo
12:50 - 09:35
ORD
-
SYD
27h 45m
2 stops
$1,488Air Canada
Mon, 2 Feb - Mon, 16 Feb
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,501Air Canada
Mon, 2 Feb - Mon, 16 Feb
Air New Zealand Logo
09:55 - 21:32
SYD
-
ORD
28h 37m
2 stops
Air New Zealand Logo
14:33 - 08:45
ORD
-
SYD
25h 12m
2 stops
$1,506Air New Zealand
Thu, 5 Feb - Fri, 20 Feb
Air Canada Logo
10:25 - 08:00
SYD
-
ORD
37h 35m
2 stops
Air Canada Logo
15:40 - 08:20
ORD
-
SYD
24h 40m
1 stop
$1,527Air Canada
Mon, 23 Mar - Tue, 31 Mar
Air Canada Logo
10:25 - 20:10
SYD
-
ORD
25h 45m
2 stops
Air Canada Logo
08:40 - 07:20
ORD
-
SYD
31h 40m
2 stops
$1,533Air Canada
Mon, 23 Mar - Mon, 6 Apr
Air Canada Logo
11:20 - 08:00
SYD
-
ORD
37h 40m
3 stops
Air Canada Logo
08:40 - 08:35
ORD
-
SYD
31h 55m
2 stops
$1,539Air Canada
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
10:40 - 17:29
SYD
-
MDW
23h 49m
2 stops
Delta Logo
13:26 - 08:30
MDW
-
SYD
26h 04m
2 stops
$1,733Delta
Mon, 2 Feb - Mon, 16 Feb
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
13:10 - 07:35
MDW
-
SYD
26h 25m
2 stops
$2,074Delta
Mon, 23 Mar - Tue, 31 Mar

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
2 Feb
SYD11:20Sydney Kingsford Smith
27h 45m
2 stops
ORD22:05Chicago O'Hare Intl
16 Feb
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD09:35Sydney Kingsford Smith
$1,483
Air Canada
2 Feb
SYD11:20Sydney Kingsford Smith
27h 45m
2 stops
ORD22:05Chicago O'Hare Intl
16 Feb
ORD12:50Chicago O'Hare Intl
27h 45m
2 stops
SYD09:35Sydney Kingsford Smith
$1,488
Air Canada
2 Feb
SYD11:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
16 Feb
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD09:35Sydney Kingsford Smith
$1,501

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets
Air New Zealand
2 Mar
SYD13:55Sydney Kingsford Smith
26h 04m
2 stops
ORD22:59Chicago O'Hare Intl
9 Mar
ORD16:00Chicago O'Hare Intl
24h 45m
2 stops
SYD08:45Sydney Kingsford Smith
$1,435
Air New Zealand
5 Feb
SYD09:55Sydney Kingsford Smith
28h 37m
2 stops
ORD21:32Chicago O'Hare Intl
20 Feb
ORD14:33Chicago O'Hare Intl
25h 12m
2 stops
SYD08:45Sydney Kingsford Smith
$1,506
Air New Zealand
8 Feb
SYD09:55Sydney Kingsford Smith
30h 04m
2 stops
ORD22:59Chicago O'Hare Intl
9 Feb
ORD14:40Chicago O'Hare Intl
26h 50m
2 stops
SYD10:30Sydney Kingsford Smith
$1,533

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 18 January 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

Mon 2/3

13:55-22:59

2 stops26h 04m

Chicago O'Hare Intl

Mon 9/3

16:00-08:45

2 stops24h 45m

$1,435

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-22:05

2 stops27h 45m

Chicago O'Hare Intl

Mon 16/2

15:35-09:35

1 stop25h 00m

$1,483

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-22:05

2 stops27h 45m

Chicago O'Hare Intl

Mon 16/2

12:50-09:35

2 stops27h 45m

$1,488

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Mon 16/2

15:35-09:35

1 stop25h 00m

$1,501

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/2

09:55-21:32

2 stops28h 37m

Chicago O'Hare Intl

Fri 20/2

14:33-08:45

2 stops25h 12m

$1,506

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 23/3

10:25-08:00

2 stops37h 35m

Chicago O'Hare Intl

Tue 31/3

15:40-08:20

1 stop24h 40m

$1,527

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 23/3

10:25-20:10

2 stops25h 45m

Chicago O'Hare Intl

Mon 6/4

08:40-07:20

2 stops31h 40m

$1,533

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

11:20-08:00

3 stops37h 40m

Chicago O'Hare Intl

Tue 10/3

08:40-08:35

2 stops31h 55m

$1,539

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40-17:29

2 stops23h 49m

Chicago Midway

Mon 16/2

13:26-08:30

2 stops26h 04m

$1,733

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 23/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Tue 31/3

13:10-07:35

2 stops26h 25m

$2,074

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

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 $1,427 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 $1,139 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 65% 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 January 2026, prices for Sydney to Chicago flights are approximately 14% 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

23h 12m

Direct flights

None
The fastest flight from Sydney to Chicago takes 23h 12m
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. 23h 12m 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 $979Free cancellationRating
7.5
972 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,166Free cancellationRating
7.2
11,154 reviews
Search American Airlines flights
Air CanadaPriceFrom $1,168Free cancellationRating
7.1
10,632 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,415Free cancellationRating
8.0
572 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,478Free cancellationRating
7.4
9,173 reviews
Search United Airlines flights
ANAPriceFrom $1,571Free cancellationRating
8.4
1,076 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