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Cheap flights from Sydney to Chicago from $776

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 22/5. 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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Find the cheapest flights from Sydney to Chicago

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 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,567Air Canada
Wed, 4 Feb - Thu, 19 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
$1,570Air Canada
Tue, 3 Feb - Wed, 18 Feb
Air New Zealand Logo
13:55 - 22:59
SYD
-
ORD
26h 04m
2 stops
Air New Zealand Logo
14:33 - 08:45
ORD
-
SYD
25h 12m
2 stops
$1,575Air New Zealand
Sun, 1 Feb - Mon, 16 Feb
Air Canada Logo
11:20 - 17:03
SYD
-
ORD
22h 43m
2 stops
Air Canada Logo
11:11 - 09:35
ORD
-
SYD
29h 24m
2 stops
$1,579Air Canada
Wed, 4 Feb - Thu, 19 Feb
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
$1,582Air Canada
Mon, 2 Feb - Tue, 17 Feb
Air Canada Logo
11:20 - 14:55
SYD
-
ORD
44h 35m
2 stops
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,584Air Canada
Thu, 29 Jan - Wed, 11 Feb
Air New Zealand Logo
09:55 - 20:25
SYD
-
ORD
27h 30m
2 stops
Air New Zealand Logo
13:00 - 08:45
ORD
-
SYD
26h 45m
2 stops
$1,603Air New Zealand
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
10:40 - 17:45
SYD
-
MDW
24h 05m
2 stops
Delta Logo
12:45 - 06:50
MDW
-
SYD
25h 05m
2 stops
$2,379Delta
Wed, 18 Feb - Sun, 1 Mar
Delta Logo
10:40 - 17:45
SYD
-
MDW
24h 05m
2 stops
Delta Logo
11:45 - 08:30
MDW
-
SYD
27h 45m
2 stops
$2,523Delta
Fri, 20 Feb - Sat, 28 Feb
Multiple Airlines Logo
14:05 - 23:13
SYD
-
MDW
26h 08m
1 stop
Multiple Airlines Logo
14:19 - 18:50
MDW
-
SYD
35h 31m
2 stops
$3,067Multiple Airlines
Sun, 1 Feb - Mon, 16 Feb

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
4 Feb
SYD11:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
19 Feb
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD09:35Sydney Kingsford Smith
$1,567
Air Canada
3 Feb
SYD11:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
18 Feb
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD09:35Sydney Kingsford Smith
$1,570
Air Canada
4 Feb
SYD11:20Sydney Kingsford Smith
22h 43m
2 stops
ORD17:03Chicago O'Hare Intl
19 Feb
ORD11:11Chicago O'Hare Intl
29h 24m
2 stops
SYD09:35Sydney Kingsford Smith
$1,579

Delta flights from Sydney to Chicago

Our best Delta deals on Sydney to Chicago flight tickets
Delta
24 Mar
SYD09:40Sydney Kingsford Smith
27h 30m
2 stops
ORD21:10Chicago O'Hare Intl
27 Apr
ORD12:45Chicago O'Hare Intl
26h 50m
2 stops
SYD06:35Sydney Kingsford Smith
$1,730
Delta
18 Feb
SYD10:40Sydney Kingsford Smith
24h 05m
2 stops
MDW17:45Chicago Midway
1 Mar
MDW12:45Chicago Midway
25h 05m
2 stops
SYD06:50Sydney Kingsford Smith
$2,379
Delta
20 Feb
SYD10:40Sydney Kingsford Smith
24h 05m
2 stops
MDW17:45Chicago Midway
28 Feb
MDW11:45Chicago Midway
27h 45m
2 stops
SYD08:30Sydney Kingsford Smith
$2,523

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 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

Wed 4/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 19/2

15:35-09:35

1 stop25h 00m

$1,567

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 18/2

15:35-09:35

1 stop25h 00m

$1,570

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 1/2

13:55-22:59

2 stops26h 04m

Chicago O'Hare Intl

Mon 16/2

14:33-08:45

2 stops25h 12m

$1,575

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 4/2

11:20-17:03

2 stops22h 43m

Chicago O'Hare Intl

Thu 19/2

11:11-09:35

2 stops29h 24m

$1,579

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 2/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Tue 17/2

07:15-09:35

2 stops33h 20m

$1,582

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

11:20-14:55

2 stops44h 35m

Chicago O'Hare Intl

Wed 11/2

15:35-09:35

1 stop25h 00m

$1,584

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/2

09:55-20:25

2 stops27h 30m

Chicago O'Hare Intl

Sun 8/2

13:00-08:45

2 stops26h 45m

$1,603

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 18/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 1/3

12:45-06:50

2 stops25h 05m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 20/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Sat 28/2

11:45-08:30

2 stops27h 45m

$2,523

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/2

14:05-23:13

1 stop26h 08m

Chicago Midway

Mon 16/2

14:19-18:50

2 stops35h 31m

$3,067

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 February, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,108.

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 $1,424 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 $1,140 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 $980Free cancellationRating
7.5
971 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,166Free cancellationRating
7.2
11,134 reviews
Search American Airlines flights
Air CanadaPriceFrom $1,169Free cancellationRating
7.1
10,623 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,415Free cancellationRating
8.0
570 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,479Free cancellationRating
7.4
9,164 reviews
Search United Airlines flights
ANAPriceFrom $1,571Free cancellationRating
8.4
1,073 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