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Cheap flights from Chicago to Sydney from $703

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sydney departing on 21/1. 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

Logo
08:05 - 08:05MDW-SYD
32h 00m2 stops
Logo
13:05 - 21:45SYD-MDW
24h 40m2 stops
$1,484
Find Deal
Tue, 21 Oct - Fri, 31 Oct
Alaska Airlines Logo
18:50 - 19:45ORD-SYD
31h 55m2 stops
Alaska Airlines Logo
21:40 - 13:04SYD-ORD
32h 24m2 stops
$1,538Alaska Airlines
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Tue, 3 Feb - Tue, 10 Feb
Logo
09:44 - 08:05MDW-SYD
30h 21m2 stops
Logo
14:05 - 23:03SYD-MDW
24h 58m2 stops
$1,558
Find Deal
Mon, 20 Oct - Sun, 2 Nov
Alaska Airlines Logo
15:15 - 19:45ORD-SYD
36h 30m2 stops
Alaska Airlines Logo
21:40 - 06:22SYD-ORD
24h 42m2 stops
$1,632Alaska Airlines
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Fri, 24 Oct - Fri, 31 Oct
Hawaiian Airlines Logo
15:15 - 19:45ORD-SYD
36h 30m2 stops
Hawaiian Airlines Logo
21:40 - 06:22SYD-ORD
24h 42m2 stops
$1,709Hawaiian Airlines
Find Deal
Fri, 24 Oct - Fri, 31 Oct
Hawaiian Airlines Logo
14:00 - 19:45ORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
21:40 - 05:04SYD-ORD
24h 24m2 stops
$1,723Hawaiian Airlines
Find Deal
Tue, 24 Feb - Sat, 7 Mar
ANA Logo
16:25 - 20:15ORD-SYD
34h 50m1 stop
ANA Logo
21:45 - 13:50SYD-ORD
33h 05m1 stop
$1,759ANA
Find Deal
Tue, 4 Nov - Tue, 18 Nov
ANA Logo
16:25 - 10:30ORD-SYD
25h 05m1 stop
ANA Logo
12:25 - 07:20SYD-ORD
35h 55m1 stop
$1,761ANA
Find Deal
Sun, 2 Nov - Tue, 18 Nov
Fiji Airways Logo
18:30 - 22:10ORD-SYD
36h 40m2 stops
Fiji Airways Logo
06:00 - 19:18SYD-ORD
30h 18m2 stops
$1,818Fiji Airways
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Tue, 23 Sep - Tue, 24 Feb
Fiji Airways Logo
17:10 - 12:30ORD-SYD
26h 20m2 stops
Fiji Airways Logo
06:00 - 19:42SYD-ORD
30h 42m2 stops
$1,824Fiji Airways
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Sat, 8 Nov - Sat, 22 Nov

Alaska Airlines flights from Chicago to Sydney

Our best Alaska Airlines deals on Chicago to Sydney flight tickets
Alaska Airlines
3 Feb
ORD18:50Chicago O'Hare Intl
31h 55m
2 stops
SYD19:45Sydney Kingsford Smith
10 Feb
SYD21:40Sydney Kingsford Smith
32h 24m
2 stops
ORD13:04Chicago O'Hare Intl
$1,538
Find similar
Alaska Airlines
24 Oct
ORD15:15Chicago O'Hare Intl
36h 30m
2 stops
SYD19:45Sydney Kingsford Smith
31 Oct
SYD21:40Sydney Kingsford Smith
24h 42m
2 stops
ORD06:22Chicago O'Hare Intl
$1,632
Find similar
Alaska Airlines
4 Nov
ORD15:25Chicago O'Hare Intl
35h 20m
2 stops
SYD19:45Sydney Kingsford Smith
18 Nov
SYD21:40Sydney Kingsford Smith
35h 50m
1 stop
ORD16:30Chicago O'Hare Intl
$1,649
Find similar

Delta flights from Chicago to Sydney

Our best Delta deals on Chicago to Sydney flight tickets
Delta
3 Nov
MDW13:48Chicago Midway
25h 42m
2 stops
SYD08:30Sydney Kingsford Smith
16 Nov
SYD10:40Sydney Kingsford Smith
24h 28m
2 stops
MDW18:08Chicago Midway
$2,218
Find similar
Delta
2 Nov
MDW13:48Chicago Midway
25h 42m
2 stops
SYD08:30Sydney Kingsford Smith
18 Nov
SYD10:40Sydney Kingsford Smith
24h 38m
2 stops
MDW18:18Chicago Midway
$2,219
Find similar
Delta
12 Nov
MDW13:47Chicago Midway
25h 43m
2 stops
SYD08:30Sydney Kingsford Smith
1 Dec
SYD10:40Sydney Kingsford Smith
40h 14m
2 stops
MDW09:54Chicago Midway
$2,248
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Chicago to Sydney 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 11 September 2025.
Use the filters below to find and compare flights from Chicago to Sydney that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 21/10

08:05-08:05

2 stops32h 00m

Sydney Kingsford Smith

Fri 31/10

13:05-21:45

2 stops24h 40m

$1,484

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 3/2

18:50-19:45

2 stops31h 55m

Sydney Kingsford Smith

Tue 10/2

21:40-13:04

2 stops32h 24m

$1,538

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 20/10

09:44-08:05

2 stops30h 21m

Sydney Kingsford Smith

Sun 2/11

14:05-23:03

2 stops24h 58m

$1,558

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Fri 24/10

15:15-19:45

2 stops36h 30m

Sydney Kingsford Smith

Fri 31/10

21:40-06:22

2 stops24h 42m

$1,632

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Fri 24/10

15:15-19:45

2 stops36h 30m

Sydney Kingsford Smith

Fri 31/10

21:40-06:22

2 stops24h 42m

$1,709

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 24/2

14:00-19:45

2 stops36h 45m

Sydney Kingsford Smith

Sat 7/3

21:40-05:04

2 stops24h 24m

$1,723

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 4/11

16:25-20:15

1 stop34h 50m

Sydney Kingsford Smith

Tue 18/11

21:45-13:50

1 stop33h 05m

$1,759

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 2/11

16:25-10:30

1 stop25h 05m

Sydney Kingsford Smith

Tue 18/11

12:25-07:20

1 stop35h 55m

$1,761

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 23/9

18:30-22:10

2 stops36h 40m

Sydney Kingsford Smith

Tue 24/2

06:00-19:18

2 stops30h 18m

$1,818

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 8/11

17:10-12:30

2 stops26h 20m

Sydney Kingsford Smith

Sat 22/11

06:00-19:42

2 stops30h 42m

$1,824

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 Sydney from

How to get the cheapest flight ticket from Chicago to Sydney

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 Chicago and Sydney?

What is the cheapest month to fly to Sydney?

The month of August is, on average, the cheapest month to fly to Sydney from Chicago, with most prices found around $1,296. If you aren’t able to travel to Sydney during the month of August, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $1,311.

What is the cheapest day to depart on your flight to Sydney?

Our data shows that Sunday is the least expensive day to fly to Sydney. Tickets to fly out on this day can be as low as $1,785. The most expensive day to fly to Sydney is Tuesday, with ticket prices averaging around $2,452.

What is the cheapest time of day to depart on your flight to Sydney?

According to our data, the cheapest time of day to fly to Sydney is in the afternoon. momondo users have found flights departing from Chicago to Sydney in the afternoon for as low as $2,089. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying at midday when prices are $3,193 on average. Flights to Sydney from Chicago at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

How far in advance should I book a flight to Sydney?

You are more likely to see cheaper flights to Sydney from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sydney for around $1,661 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sydney from Chicago for as low as $1,310 on momondo.

Can stopping save me money on Chicago to Sydney flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago to Sydney flight.

How have Chicago to Sydney flight prices changed over time?

As of September 2025, prices for Chicago to Sydney flights are approximately 65% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Sydney

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Sydney according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Chicago to Sydney (CHI to SYD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Sydney

Direct flights

None
There are no direct flights from Chicago to Sydney. There are no popular flight routes from Chicago to Sydney.
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  • How far is Chicago to Sydney Kingsford Smith by plane?

    Chicago and Sydney Kingsford Smith are 14866.2 km apart from one another. A reasonable flight in good conditions will take 25h 05m.

  • When did momondo last update prices for flights from Chicago to Sydney Kingsford Smith Airport?

    Prices for flights from Chicago to Sydney Kingsford Smith Airport were last updated today.

  • How many operators does momondo search for flights from Chicago to Sydney Kingsford Smith Airport?

  • How old do you have to be to fly from Chicago to Sydney Kingsford Smith Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and stopovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Sydney Kingsford Smith Airport.

  • What documentation or ID do you need to fly to Sydney Kingsford Smith Airport?

    The necessary travel and health documents for your Sydney Kingsford Smith Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's licence and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to Sydney?

Best airlines flying from Chicago to Sydney

Compare and see reviews for airlines that fly from Chicago to Sydney with momondo
Airline
Rating
Free cancellation
Price
Air CanadaPriceFrom $1,258Free cancellationRating
7.1
10,000 reviews
Search Air Canada flights
Qantas AirwaysPriceFrom $1,322Free cancellationRating
7.5
905 reviews
Search Qantas Airways flights

Travelling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Terrigal
Penrith
Katoomba
Lithgow
Leura
Manly
Bondi Beach
Coogee
Randwick
Cronulla
Charlestown
Newport
Swansea

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sydney?

It is quick and easy to find Chicago to Sydney flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Sydney that suits you.

Can I find flights from Chicago to Sydney with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Sydney from Chicago with this policy.

How can momondo help me find flights from Chicago to Sydney?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Sydney from Chicago.

I’m not ready to book a flight from Chicago to Sydney right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Sydney, momondo offers a useful price alert feature which will track prices for flights to Sydney from Chicago and alert you when they change.

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