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Cheap flights from Sydney to Chicago from $874

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 17/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap return flights

Enter your travel dates to find the best prices.
Air Canada Logo
09:20 - 14:45
SYD
-
ORD
20h 25m
1 stop
Air Canada Logo
08:40 - 07:20
ORD
-
SYD
31h 40m
2 stops
$1,269Air Canada
Thu, 16 Apr - Wed, 29 Apr
Air Canada Logo
09:20 - 14:45
SYD
-
ORD
20h 25m
1 stop
Air Canada Logo
15:40 - 07:20
ORD
-
SYD
24h 40m
1 stop
$1,273Air Canada
Mon, 20 Apr - Thu, 30 Apr
Air Canada Logo
09:20 - 20:05
SYD
-
ORD
25h 45m
2 stops
Air Canada Logo
09:50 - 07:20
ORD
-
SYD
30h 30m
2 stops
$1,279Air Canada
Mon, 20 Apr - Thu, 30 Apr
Multiple Airlines Logo
13:15 - 05:35
SYD
-
ORD
31h 20m
2 stops
Multiple Airlines Logo
05:15 - 11:50
ORD
-
SYD
39h 35m
2 stops
$1,287Multiple Airlines
Sun, 3 May - Sun, 10 May
Air Canada Logo
09:20 - 13:05
SYD
-
ORD
42h 45m
2 stops
Air Canada Logo
08:40 - 07:20
ORD
-
SYD
31h 40m
2 stops
$1,289Air Canada
Thu, 16 Apr - Wed, 29 Apr
Multiple Airlines Logo
13:15 - 23:27
SYD
-
ORD
25h 12m
2 stops
Multiple Airlines Logo
14:00 - 11:50
ORD
-
SYD
30h 50m
2 stops
$1,297Multiple Airlines
Wed, 15 Apr - Thu, 16 Apr
Air Canada Logo
09:20 - 14:45
SYD
-
ORD
20h 25m
1 stop
Air Canada Logo
15:40 - 07:20
ORD
-
SYD
24h 40m
1 stop
$1,304Air Canada
Thu, 16 Apr - Wed, 29 Apr
Delta Logo
09:15 - 17:58
SYD
-
MDW
23h 43m
2 stops
Delta Logo
12:52 - 06:50
MDW
-
SYD
26h 58m
2 stops
$2,122Delta
Wed, 29 Apr - Wed, 6 May
Delta Logo
09:15 - 17:58
SYD
-
MDW
23h 43m
2 stops
Delta Logo
13:24 - 06:50
MDW
-
SYD
26h 26m
2 stops
$2,137Delta
Tue, 28 Apr - Tue, 5 May
Delta Logo
09:15 - 18:36
SYD
-
MDW
24h 21m
2 stops
Delta Logo
13:22 - 06:50
MDW
-
SYD
26h 28m
2 stops
$2,194Delta
Thu, 30 Apr - Thu, 7 May

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
16 Apr
SYD09:20Sydney Kingsford Smith
20h 25m
1 stop
ORD14:45Chicago O'Hare Intl
29 Apr
ORD08:40Chicago O'Hare Intl
31h 40m
2 stops
SYD07:20Sydney Kingsford Smith
$1,269
Air Canada
20 Apr
SYD09:20Sydney Kingsford Smith
22h 15m
2 stops
ORD16:35Chicago O'Hare Intl
30 Apr
ORD15:40Chicago O'Hare Intl
24h 40m
1 stop
SYD07:20Sydney Kingsford Smith
$1,273
Air Canada
16 Apr
SYD09:20Sydney Kingsford Smith
20h 25m
1 stop
ORD14:45Chicago O'Hare Intl
23 Apr
ORD08:40Chicago O'Hare Intl
31h 40m
2 stops
SYD07:20Sydney Kingsford Smith
$1,278

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets
American Airlines
25 Mar
SYD11:20Sydney Kingsford Smith
24h 20m
2 stops
ORD19:40Chicago O'Hare Intl
23 Apr
ORD19:21Chicago O'Hare Intl
20h 44m
1 stop
SYD07:05Sydney Kingsford Smith
$2,904
American Airlines
25 Mar
SYD11:20Sydney Kingsford Smith
24h 20m
2 stops
ORD19:40Chicago O'Hare Intl
31 Mar
ORD16:44Chicago O'Hare Intl
25h 01m
2 stops
SYD09:45Sydney Kingsford Smith
$2,966
American Airlines
25 Mar
SYD11:20Sydney Kingsford Smith
24h 20m
2 stops
ORD19:40Chicago O'Hare Intl
23 Apr
ORD17:25Chicago O'Hare Intl
22h 40m
2 stops
SYD07:05Sydney Kingsford Smith
$3,007

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 19 March 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 16/4

09:20-14:45

1 stop20h 25m

Chicago O'Hare Intl

Wed 29/4

08:40-07:20

2 stops31h 40m

$1,269
Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 20/4

09:20-14:45

1 stop20h 25m

Chicago O'Hare Intl

Thu 30/4

15:40-07:20

1 stop24h 40m

$1,273

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 20/4

09:20-20:05

2 stops25h 45m

Chicago O'Hare Intl

Thu 30/4

09:50-07:20

2 stops30h 30m

$1,279

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 3/5

13:15-05:35

2 stops31h 20m

Chicago O'Hare Intl

Sun 10/5

05:15-11:50

2 stops39h 35m

$1,287

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 16/4

09:20-13:05

2 stops42h 45m

Chicago O'Hare Intl

Wed 29/4

08:40-07:20

2 stops31h 40m

$1,289

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 15/4

13:15-23:27

2 stops25h 12m

Chicago O'Hare Intl

Thu 16/4

14:00-11:50

2 stops30h 50m

$1,297

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 16/4

09:20-14:45

1 stop20h 25m

Chicago O'Hare Intl

Wed 29/4

15:40-07:20

1 stop24h 40m

$1,304

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 29/4

09:15-17:58

2 stops23h 43m

Chicago Midway

Wed 6/5

12:52-06:50

2 stops26h 58m

$2,122

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 28/4

09:15-17:58

2 stops23h 43m

Chicago Midway

Tue 5/5

13:24-06:50

2 stops26h 26m

$2,137

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/4

09:15-18:36

2 stops24h 21m

Chicago Midway

Thu 7/5

13:22-06:50

2 stops26h 28m

$2,194

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 August, then you should wait until July to fly from Sydney, when ticket prices are also cheap, with an average price of $1,550.

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 $1,806 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 $1,183 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 1% 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 March 2026, prices for Sydney to Chicago flights are approximately 1% 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

21h 09m

Direct flights

None
The fastest flight from Sydney to Chicago takes 21h 09m
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. 21h 09m 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 $1,068Free cancellationRating
7.5
1,006 reviews
Search Qantas Airways flights
Air CanadaPriceFrom $1,070Free cancellationRating
7.1
10,816 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,101Free cancellationRating
7.1
11,477 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,336Free cancellationRating
8.0
615 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,396Free cancellationRating
7.4
9,443 reviews
Search United Airlines flights
ANAPriceFrom $1,483Free cancellationRating
8.4
1,131 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