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Cheap flights from Chicago to Sydney from $527

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 10/25. 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
0 bags

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Find the cheapest flights from Chicago to Sydney

Cheap round-trip flights

Multiple Airlines Logo
12:03 pm - 9:00 amMDW-SYD
28h 57m2 stops
Multiple Airlines Logo
2:05 pm - 10:03 pmSYD-MDW
24h 58m2 stops
$1,033Multiple Airlines
Find Deal
Mon, Oct 27 - Sun, Nov 9
Multiple Airlines Logo
9:44 am - 8:05 amMDW-SYD
30h 21m2 stops
Multiple Airlines Logo
2:05 pm - 11:03 pmSYD-MDW
24h 58m2 stops
$1,072Multiple Airlines
Find Deal
Mon, Oct 20 - Sun, Nov 2
Fiji Airways Logo
4:45 pm - 12:30 pmORD-SYD
26h 45m2 stops
Fiji Airways Logo
2:10 pm - 7:18 pmSYD-ORD
22h 08m2 stops
$1,102Fiji Airways
Find Deal
Sat, Feb 28 - Sat, Mar 7
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
ANA Logo
12:25 pm - 8:54 amSYD-ORD
37h 29m2 stops
$1,129ANA
Find Deal
Mon, Feb 16 - Sun, Mar 1
Hawaiian Airlines Logo
2:00 pm - 7:45 pmORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
9:40 pm - 1:04 pmSYD-ORD
32h 24m2 stops
$1,135Hawaiian Airlines
Find Deal
Tue, Feb 17 - Tue, Mar 3
Hawaiian Airlines Logo
2:00 pm - 7:45 pmORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
9:40 pm - 1:04 pmSYD-ORD
31h 24m2 stops
$1,136Hawaiian Airlines
Find Deal
Tue, Feb 24 - Tue, Mar 10
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
ANA Logo
12:25 pm - 9:37 amSYD-ORD
37h 12m2 stops
$1,144ANA
Find Deal
Tue, Mar 3 - Wed, Mar 18
Fiji Airways Logo
4:45 pm - 12:30 pmORD-SYD
26h 45m2 stops
Fiji Airways Logo
2:10 pm - 7:18 pmSYD-ORD
22h 08m2 stops
$1,167Fiji Airways
Find Deal
Sat, Feb 7 - Sat, Feb 14
Delta Logo
12:47 pm - 8:30 amMDW-SYD
26h 43m2 stops
Delta Logo
10:40 am - 4:38 pmSYD-MDW
22h 58m2 stops
$1,467Delta
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Mon, Nov 10 - Sun, Nov 23
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
Delta Logo
9:40 am - 6:08 pmSYD-MDW
24h 28m2 stops
$1,468Delta
Find Deal
Mon, Feb 9 - Sun, Mar 22

ANA flights from Chicago to Sydney

Our best ANA deals on Chicago to Sydney flight tickets
ANA
Feb 16
ORD4:25 pmChicago O'Hare Intl
34h 50m
1 stop
SYD8:15 pmSydney Kingsford Smith
Mar 1
SYD12:25 pmSydney Kingsford Smith
37h 29m
2 stops
ORD8:54 amChicago O'Hare Intl
$1,129
Find similar
ANA
Mar 3
ORD4:25 pmChicago O'Hare Intl
34h 50m
1 stop
SYD8:15 pmSydney Kingsford Smith
Mar 18
SYD12:25 pmSydney Kingsford Smith
37h 12m
2 stops
ORD9:37 amChicago O'Hare Intl
$1,144
Find similar
ANA
Mar 3
ORD7:10 amChicago O'Hare Intl
44h 05m
2 stops
SYD8:15 pmSydney Kingsford Smith
Mar 18
SYD12:25 pmSydney Kingsford Smith
37h 12m
2 stops
ORD9:37 amChicago O'Hare Intl
$1,148
Find similar

Hawaiian Airlines flights from Chicago to Sydney

Our best Hawaiian Airlines deals on Chicago to Sydney flight tickets
Hawaiian Airlines
Feb 17
ORD2:00 pmChicago O'Hare Intl
36h 45m
2 stops
SYD7:45 pmSydney Kingsford Smith
Mar 3
SYD9:40 pmSydney Kingsford Smith
32h 24m
2 stops
ORD1:04 pmChicago O'Hare Intl
$1,135
Find similar
Hawaiian Airlines
Feb 24
ORD2:00 pmChicago O'Hare Intl
36h 45m
2 stops
SYD7:45 pmSydney Kingsford Smith
Mar 10
SYD9:40 pmSydney Kingsford Smith
31h 24m
2 stops
ORD1:04 pmChicago O'Hare Intl
$1,136
Find similar
Hawaiian Airlines
Feb 4
ORD2:00 pmChicago O'Hare Intl
36h 45m
2 stops
SYD7:45 pmSydney Kingsford Smith
Feb 13
SYD9:40 pmSydney Kingsford Smith
32h 24m
2 stops
ORD1:04 pmChicago O'Hare Intl
$1,156
Find similar

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated September 17, 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

Mon 10/27

12:03 pm-9:00 am

2 stops28h 57m

Sydney Kingsford Smith

Sun 11/9

2:05 pm-10:03 pm

2 stops24h 58m

$1,033

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 10/20

9:44 am-8:05 am

2 stops30h 21m

Sydney Kingsford Smith

Sun 11/2

2:05 pm-11:03 pm

2 stops24h 58m

$1,072

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 2/28

4:45 pm-12:30 pm

2 stops26h 45m

Sydney Kingsford Smith

Sat 3/7

2:10 pm-7:18 pm

2 stops22h 08m

$1,102

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 2/16

4:25 pm-8:15 pm

1 stop34h 50m

Sydney Kingsford Smith

Sun 3/1

12:25 pm-8:54 am

2 stops37h 29m

$1,129

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/17

2:00 pm-7:45 pm

2 stops36h 45m

Sydney Kingsford Smith

Tue 3/3

9:40 pm-1:04 pm

2 stops32h 24m

$1,135

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/24

2:00 pm-7:45 pm

2 stops36h 45m

Sydney Kingsford Smith

Tue 3/10

9:40 pm-1:04 pm

2 stops31h 24m

$1,136

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 3/3

4:25 pm-8:15 pm

1 stop34h 50m

Sydney Kingsford Smith

Wed 3/18

12:25 pm-9:37 am

2 stops37h 12m

$1,144

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 2/7

4:45 pm-12:30 pm

2 stops26h 45m

Sydney Kingsford Smith

Sat 2/14

2:10 pm-7:18 pm

2 stops22h 08m

$1,167

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 11/10

12:47 pm-8:30 am

2 stops26h 43m

Sydney Kingsford Smith

Sun 11/23

10:40 am-4:38 pm

2 stops22h 58m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 2/9

1:00 pm-8:30 am

2 stops26h 30m

Sydney Kingsford Smith

Sun 3/22

9:40 am-6:08 pm

2 stops24h 28m

$1,468

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

In general, August is the cheapest month to fly from Chicago to Sydney. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $851. If you are unable to visit Sydney during the month of August, then departing from Chicago during the month May is also very affordable. Most momondo users find prices during this month for around $867.

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

The cheapest day to depart from Chicago to Sydney is on a Saturday when prices can be found for as low as $1,166. The most expensive day to fly to Sydney is Thursday, with ticket prices averaging around $1,391.

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 morning. momondo users have found flights departing from Chicago to Sydney in the morning for as low as $1,224. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Sydney are more costly in the evening, with an average ticket price of $1,412. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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 $1,105 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sydney from Chicago for as low as $859 on momondo.

Can stopping save me money on Chicago to Sydney flights?

You could potentially save up to 9% 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 round-trip 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?

    There are 9237.5 mi between Chicago and Sydney Kingsford Smith. By plane, this route typically takes 24h 30m.

  • 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 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 Chicago to Sydney Kingsford Smith Airport.

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

    The required travel and health documents for your Sydney Kingsford Smith Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Sydney Kingsford Smith Airport. We recommend that you seek guidance from your airline or a reliable 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
ANAPriceFrom $679Free CancellationRating
8.4
964 reviews
Search ANA flights
Qantas AirwaysPriceFrom $812Free CancellationRating
7.5
907 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $823Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $846Free CancellationRating
7.9
7,961 reviews
Search Delta flights
Fiji AirwaysPriceFrom $849Free CancellationRating
8.0
205 reviews
Search Fiji Airways flights
Air CanadaPriceFrom $959Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,282Free CancellationRating
8.0
505 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,336Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

Traveling to a place near Sydney?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Sydney for 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 for Chicago to Sydney flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Chicago to Sydney flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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