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Cheap flights from Sydney to Chicago from $649

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 29/8. 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.
Multiple Airlines Logo
13:15 - 06:08
SYD
-
ORD
31h 53m
3 stops
Multiple Airlines Logo
12:40 - 11:50
ORD
-
SYD
32h 10m
3 stops
$1,518Multiple Airlines
Wed, 29 Apr - Tue, 5 May
Multiple Airlines Logo
13:15 - 23:27
SYD
-
ORD
25h 12m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
2 stops
$1,538Multiple Airlines
Tue, 28 Apr - Mon, 4 May
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
12:40 - 22:10
ORD
-
SYD
42h 30m
3 stops
$1,539Multiple Airlines
Wed, 29 Apr - Tue, 5 May
Multiple Airlines Logo
13:15 - 05:59
SYD
-
ORD
31h 44m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
2 stops
$1,580Multiple Airlines
Sun, 24 May - Sun, 31 May
Multiple Airlines Logo
13:20 - 05:59
SYD
-
ORD
31h 39m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
2 stops
$1,606Multiple Airlines
Wed, 3 Jun - Fri, 12 Jun
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
12:40 - 22:10
ORD
-
SYD
42h 30m
3 stops
$1,607Multiple Airlines
Mon, 27 Apr - Tue, 12 May
Multiple Airlines Logo
06:00 - 06:08
SYD
-
ORD
39h 08m
3 stops
Multiple Airlines Logo
05:20 - 22:10
ORD
-
SYD
49h 50m
3 stops
$1,660Multiple Airlines
Tue, 28 Apr - Mon, 4 May
Multiple Airlines Logo
06:00 - 06:19
SYD
-
ORD
39h 19m
2 stops
Multiple Airlines Logo
06:55 - 22:10
ORD
-
SYD
48h 15m
3 stops
$1,666Multiple Airlines
Mon, 27 Jul - Tue, 4 Aug
Delta Logo
09:15 - 17:56
SYD
-
MDW
23h 41m
2 stops
Delta Logo
13:22 - 06:50
MDW
-
SYD
26h 28m
2 stops
$2,326Delta
Tue, 19 May - Tue, 26 May
Delta Logo
09:15 - 21:09
SYD
-
MDW
26h 54m
2 stops
Delta Logo
13:22 - 06:50
MDW
-
SYD
26h 28m
2 stops
$2,330Delta
Tue, 19 May - Tue, 26 May

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
10 July
SYD20:55Sydney Kingsford Smith
26h 45m
1 stop
ORD08:40Chicago O'Hare Intl
26 July
ORD08:46Chicago O'Hare Intl
43h 24m
2 stops
SYD19:10Sydney Kingsford Smith
$1,851
ANA
13 July
SYD20:55Sydney Kingsford Smith
26h 45m
1 stop
ORD08:40Chicago O'Hare Intl
10 Aug
ORD20:18Chicago O'Hare Intl
46h 07m
2 stops
SYD09:25Sydney Kingsford Smith
$1,905
ANA
9 June
SYD11:45Sydney Kingsford Smith
32h 06m
2 stops
ORD04:51Chicago O'Hare Intl
7 July
ORD17:45Chicago O'Hare Intl
34h 25m
1 stop
SYD19:10Sydney Kingsford Smith
$1,908

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
18 Apr
SYD09:10Sydney Kingsford Smith
29h 49m
1 stop
ORD23:59Chicago O'Hare Intl
30 Apr
ORD19:21Chicago O'Hare Intl
20h 44m
1 stop
SYD07:05Sydney Kingsford Smith
$2,794
Qantas Airways
16 Apr
SYD09:10Sydney Kingsford Smith
20h 06m
1 stop
ORD14:16Chicago O'Hare Intl
19 Apr
ORD08:05Chicago O'Hare Intl
31h 20m
1 stop
SYD06:25Sydney Kingsford Smith
$2,819
Qantas Airways
13 Apr
SYD09:10Sydney Kingsford Smith
20h 06m
1 stop
ORD14:16Chicago O'Hare Intl
13 Apr
ORD19:21Chicago O'Hare Intl
20h 44m
1 stop
SYD07:05Sydney Kingsford Smith
$4,658

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 10 April 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

Wed 29/4

13:15-06:08

3 stops31h 53m

Chicago O'Hare Intl

Tue 5/5

12:40-11:50

3 stops32h 10m

$1,518

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 28/4

13:15-23:27

2 stops25h 12m

Chicago O'Hare Intl

Mon 4/5

07:15-11:50

2 stops37h 35m

$1,538

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 29/4

13:15-05:50

2 stops31h 35m

Chicago O'Hare Intl

Tue 5/5

12:40-22:10

3 stops42h 30m

$1,539

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 24/5

13:15-05:59

2 stops31h 44m

Chicago O'Hare Intl

Sun 31/5

07:15-11:50

2 stops37h 35m

$1,580

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 3/6

13:20-05:59

2 stops31h 39m

Chicago O'Hare Intl

Fri 12/6

07:15-11:50

2 stops37h 35m

$1,606

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 27/4

13:15-05:50

2 stops31h 35m

Chicago O'Hare Intl

Tue 12/5

12:40-22:10

3 stops42h 30m

$1,607

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 28/4

06:00-06:08

3 stops39h 08m

Chicago O'Hare Intl

Mon 4/5

05:20-22:10

3 stops49h 50m

$1,660

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 27/7

06:00-06:19

2 stops39h 19m

Chicago O'Hare Intl

Tue 4/8

06:55-22:10

3 stops48h 15m

$1,666
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 19/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Tue 26/5

13:22-06:50

2 stops26h 28m

$2,326

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 19/5

09:15-21:09

2 stops26h 54m

Chicago Midway

Tue 26/5

13:22-06:50

2 stops26h 28m

$2,330

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 February to fly from Sydney, when ticket prices are also cheap, with an average price of $1,586.

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 $1,876 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 $1,399 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 18% 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 April 2026, prices for Sydney to Chicago flights are approximately 84% more expensive 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

20h 11m

Direct flights

None
The fastest flight from Sydney to Chicago takes 20h 11m
There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.
Search flight deals

Frequently asked questions about flying from Sydney to Chicago

  • How far is Sydney Kingsford Smith to Chicago by plane?

    There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 11m 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
Air CanadaPriceFrom $1,074Free cancellationRating
7.1
10,915 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,105Free cancellationRating
7.1
11,562 reviews
Search American Airlines flights
Qantas AirwaysPriceFrom $1,251Free cancellationRating
7.5
1,018 reviews
Search Qantas Airways flights
Air New ZealandPriceFrom $1,341Free cancellationRating
8.0
626 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,402Free cancellationRating
7.4
9,561 reviews
Search United Airlines flights
ANAPriceFrom $1,489Free cancellationRating
8.4
1,170 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