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Cheap flights from Sydney to Chicago from $664

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 16/3. 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
09:55 - 20:23
SYD
-
ORD
26h 28m
2 stops
Air New Zealand Logo
16:00 - 10:30
ORD
-
SYD
26h 30m
2 stops
$1,493Air New Zealand
Tue, 10 Mar - Tue, 17 Mar
Air New Zealand Logo
11:45 - 20:23
SYD
-
ORD
24h 38m
2 stops
Air New Zealand Logo
14:35 - 08:45
ORD
-
SYD
26h 10m
2 stops
$1,494Air New Zealand
Tue, 10 Mar - Tue, 17 Mar
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
$1,516Air Canada
Tue, 10 Mar - Tue, 17 Mar
Air Canada Logo
10:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
15:35 - 08:35
ORD
-
SYD
25h 00m
1 stop
$1,543Air Canada
Tue, 10 Mar - Tue, 17 Mar
Air New Zealand Logo
11:45 - 23:08
SYD
-
ORD
27h 23m
2 stops
Air New Zealand Logo
16:00 - 10:30
ORD
-
SYD
26h 30m
2 stops
$1,632Air New Zealand
Thu, 12 Mar - Thu, 19 Mar
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
07:15 - 09:35
ORD
-
SYD
33h 20m
2 stops
$1,649Air Canada
Sat, 21 Feb - Sat, 28 Feb
Air Canada Logo
11:20 - 20:10
SYD
-
ORD
25h 50m
2 stops
Air Canada Logo
07:15 - 09:35
ORD
-
SYD
33h 20m
2 stops
$1,655Air Canada
Sat, 21 Feb - Sat, 28 Feb
American Airlines Logo
11:20 - 17:46
SYD
-
ORD
23h 26m
1 stop
American Airlines Logo
14:33 - 09:00
ORD
-
SYD
25h 27m
1 stop
$1,691American Airlines
Mon, 16 Feb - Wed, 4 Mar
Delta Logo
10:40 - 18:40
SYD
-
MDW
25h 00m
2 stops
Delta Logo
09:34 - 08:30
MDW
-
SYD
29h 56m
2 stops
$1,998Delta
Mon, 16 Feb - Wed, 4 Mar
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
13:00 - 06:50
MDW
-
SYD
26h 50m
2 stops
$2,136Delta
Fri, 26 Jun - Wed, 15 Jul

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
16 Feb
SYD11:20Sydney Kingsford Smith
20h 33m
1 stop
ORD14:53Chicago O'Hare Intl
3 Mar
ORD16:45Chicago O'Hare Intl
23h 15m
1 stop
SYD09:00Sydney Kingsford Smith
$1,697
Qantas Airways
7 Mar
SYD11:20Sydney Kingsford Smith
20h 33m
1 stop
ORD14:53Chicago O'Hare Intl
28 Mar
ORD21:30Chicago O'Hare Intl
42h 35m
1 stop
SYD08:05Sydney Kingsford Smith
$1,786
Qantas Airways
10 July
SYD09:10Sydney Kingsford Smith
20h 08m
1 stop
ORD14:18Chicago O'Hare Intl
26 July
ORD11:49Chicago O'Hare Intl
28h 16m
1 stop
SYD07:05Sydney Kingsford Smith
$1,943

United Airlines flights from Sydney to Chicago

Our best United Airlines deals on Sydney to Chicago flight tickets
United Airlines
16 Feb
SYD11:50Sydney Kingsford Smith
19h 53m
1 stop
ORD14:43Chicago O'Hare Intl
4 Mar
ORD14:35Chicago O'Hare Intl
25h 30m
2 stops
SYD09:05Sydney Kingsford Smith
$1,717
United Airlines
16 Feb
SYD12:10Sydney Kingsford Smith
19h 35m
1 stop
ORD14:45Chicago O'Hare Intl
3 Mar
ORD14:35Chicago O'Hare Intl
25h 30m
2 stops
SYD09:05Sydney Kingsford Smith
$1,720
United Airlines
15 Feb
SYD11:20Sydney Kingsford Smith
22h 45m
2 stops
ORD17:05Chicago O'Hare Intl
2 Mar
ORD16:00Chicago O'Hare Intl
22h 00m
1 stop
SYD07:00Sydney Kingsford Smith
$1,789

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 28 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

Tue 10/3

09:55-20:23

2 stops26h 28m

Chicago O'Hare Intl

Tue 17/3

16:00-10:30

2 stops26h 30m

$1,493

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

11:45-20:23

2 stops24h 38m

Chicago O'Hare Intl

Tue 17/3

14:35-08:45

2 stops26h 10m

$1,494

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 17/3

10:35-08:35

2 stops30h 00m

$1,516

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 17/3

15:35-08:35

1 stop25h 00m

$1,543

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 12/3

11:45-23:08

2 stops27h 23m

Chicago O'Hare Intl

Thu 19/3

16:00-10:30

2 stops26h 30m

$1,632

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 21/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Sat 28/2

07:15-09:35

2 stops33h 20m

$1,649

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 21/2

11:20-20:10

2 stops25h 50m

Chicago O'Hare Intl

Sat 28/2

07:15-09:35

2 stops33h 20m

$1,655

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 16/2

11:20-17:46

1 stop23h 26m

Chicago O'Hare Intl

Wed 4/3

14:33-09:00

1 stop25h 27m

$1,691

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 16/2

10:40-18:40

2 stops25h 00m

Chicago Midway

Wed 4/3

09:34-08:30

2 stops29h 56m

$1,998

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Wed 15/7

13:00-06:50

2 stops26h 50m

$2,136

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 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 $1,087.

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 $1,380 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 $1,097 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

19h 45m

Direct flights

None
The fastest flight from Sydney to Chicago takes 19h 45m
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. 19h 45m 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 $946Free cancellationRating
7.5
980 reviews
Search Qantas Airways flights
Air CanadaPriceFrom $1,091Free cancellationRating
7.1
10,666 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,122Free cancellationRating
7.2
11,199 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,362Free cancellationRating
8.0
577 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,423Free cancellationRating
7.4
9,215 reviews
Search United Airlines flights
ANAPriceFrom $1,512Free cancellationRating
8.4
1,078 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