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Cheap flights from Sydney to Chicago from $882

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 27/4. 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
10:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
15:35 - 08:35
ORD
-
SYD
25h 00m
1 stop
$1,349Air Canada
Tue, 10 Mar - Wed, 25 Mar
Air Canada Logo
10:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
07:15 - 08:35
ORD
-
SYD
33h 20m
2 stops
$1,357Air Canada
Wed, 11 Mar - Thu, 26 Mar
Air Canada Logo
10:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
08:00 - 08:35
ORD
-
SYD
32h 35m
2 stops
$1,364Air Canada
Tue, 10 Mar - Wed, 25 Mar
Air Canada Logo
10:20 - 19:45
SYD
-
ORD
25h 25m
2 stops
Air Canada Logo
10:00 - 08:35
ORD
-
SYD
30h 35m
2 stops
$1,367Air Canada
Tue, 10 Mar - Wed, 25 Mar
Air Canada Logo
10:20 - 13:01
SYD
-
ORD
42h 41m
2 stops
Air Canada Logo
13:55 - 08:35
ORD
-
SYD
26h 40m
2 stops
$1,380Air Canada
Wed, 11 Mar - Thu, 26 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
$1,390Air Canada
Wed, 11 Mar - Thu, 26 Mar
Air Canada Logo
11:20 - 22:04
SYD
-
ORD
27h 44m
2 stops
Air Canada Logo
06:17 - 08:35
ORD
-
SYD
34h 18m
2 stops
$1,422Air Canada
Wed, 4 Mar - Tue, 10 Mar
Air Canada Logo
11:20 - 08:00
SYD
-
ORD
37h 40m
2 stops
Air Canada Logo
21:15 - 08:35
ORD
-
SYD
43h 20m
2 stops
$1,433Air Canada
Wed, 4 Mar - Sun, 15 Mar
Delta Logo
10:40 - 17:45
SYD
-
MDW
24h 05m
2 stops
Delta Logo
13:10 - 06:05
MDW
-
SYD
24h 55m
2 stops
$1,500Delta
Wed, 4 Mar - Sun, 15 Mar
Delta Logo
09:15 - 18:14
SYD
-
MDW
23h 59m
2 stops
Delta Logo
09:20 - 06:50
MDW
-
SYD
30h 30m
2 stops
$1,549Delta
Mon, 1 Jun - Fri, 31 Jul

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
12 June
SYD17:50Sydney Kingsford Smith
21h 09m
1 stop
ORD23:59Chicago O'Hare Intl
12 July
ORD18:02Chicago O'Hare Intl
21h 53m
1 stop
SYD06:55Sydney Kingsford Smith
$1,559
Qantas Airways
3 June
SYD09:10Sydney Kingsford Smith
21h 42m
1 stop
ORD15:52Chicago O'Hare Intl
22 June
ORD21:04Chicago O'Hare Intl
42h 21m
1 stop
SYD06:25Sydney Kingsford Smith
$1,572

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
11 Mar
SYD10:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
26 Mar
ORD07:15Chicago O'Hare Intl
33h 20m
2 stops
SYD08:35Sydney Kingsford Smith
$1,357
Air Canada
11 Mar
SYD10:20Sydney Kingsford Smith
42h 41m
2 stops
ORD13:01Chicago O'Hare Intl
26 Mar
ORD13:55Chicago O'Hare Intl
26h 40m
2 stops
SYD08:35Sydney Kingsford Smith
$1,380
Air Canada
11 Mar
SYD10:20Sydney Kingsford Smith
20h 21m
1 stop
ORD14:41Chicago O'Hare Intl
26 Mar
ORD15:35Chicago O'Hare Intl
25h 00m
1 stop
SYD08:35Sydney Kingsford Smith
$1,390

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 22 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

Tue 10/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 25/3

15:35-08:35

1 stop25h 00m

$1,349

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 26/3

07:15-08:35

2 stops33h 20m

$1,357

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 25/3

08:00-08:35

2 stops32h 35m

$1,364

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/3

10:20-19:45

2 stops25h 25m

Chicago O'Hare Intl

Wed 25/3

10:00-08:35

2 stops30h 35m

$1,367

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/3

10:20-13:01

2 stops42h 41m

Chicago O'Hare Intl

Thu 26/3

13:55-08:35

2 stops26h 40m

$1,380

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/3

10:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 26/3

15:35-08:35

1 stop25h 00m

$1,390

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 4/3

11:20-22:04

2 stops27h 44m

Chicago O'Hare Intl

Tue 10/3

06:17-08:35

2 stops34h 18m

$1,422

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 4/3

11:20-08:00

2 stops37h 40m

Chicago O'Hare Intl

Sun 15/3

21:15-08:35

2 stops43h 20m

$1,433

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 4/3

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 15/3

13:10-06:05

2 stops24h 55m

$1,500

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/6

09:15-18:14

2 stops23h 59m

Chicago Midway

Fri 31/7

09:20-06:50

2 stops30h 30m

$1,549

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 April, then you should wait until March to fly from Sydney, when ticket prices are also cheap, with an average price of $1,216.

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 $1,688 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 $1,131 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

19h 34m

Direct flights

None
The fastest flight from Sydney to Chicago takes 19h 34m
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 34m 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 $927Free cancellationRating
7.5
997 reviews
Search Qantas Airways flights
Air CanadaPriceFrom $1,069Free cancellationRating
7.1
10,739 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,100Free cancellationRating
7.2
11,341 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,335Free cancellationRating
8.0
597 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,395Free cancellationRating
7.4
9,341 reviews
Search United Airlines flights
ANAPriceFrom $1,482Free cancellationRating
8.4
1,098 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