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$459+ Cheap flights from Chicago (CHI) to Sydney (SYD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap flight deals from Chicago to Sydney

Cheapest flights from Chicago to Sydney
Explore the most affordable flight options available from Chicago to Sydney. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2026.

This Trip.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:30 am
ORD
-
SYD
2 stops37h 20m
Multiple Airlines
Tue 4/281:15 pm
SYD
-
ORD
2 stops25h 12m
Multiple Airlines
Deal found 3/25$971
This Trip.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:30 am
ORD
-
SYD
2 stops37h 20m
Multiple Airlines
Wed 6/31:20 pm
SYD
-
ORD
2 stops31h 15m
Multiple Airlines
Deal found 3/25$983
This Trip.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:55 am
ORD
-
SYD
3 stops37h 55m
Multiple Airlines
Sat 5/166:00 am
SYD
-
ORD
3 stops56h 13m
Multiple Airlines
Deal found 3/27$1,007
This Trip.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:39 pm
ORD
-
SYD
2 stops30h 26m
Multiple Airlines
Mon 6/11:15 pm
SYD
-
ORD
2 stops25h 12m
Multiple Airlines
Deal found 3/24$1,040
This Trip.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:00 pm
ORD
-
SYD
2 stops30h 50m
Multiple Airlines
Sun 5/31:15 pm
SYD
-
ORD
2 stops31h 20m
Multiple Airlines
Deal found 3/27$1,071
This Mytrip deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:39 pm
ORD
-
SYD
2 stops30h 11m
Multiple Airlines
Thu 5/146:00 am
SYD
-
ORD
2 stops32h 27m
Multiple Airlines
Deal found 3/23$1,098
This Trip.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:20 am
ORD
-
SYD
3 stops49h 50m
Multiple Airlines
Thu 5/141:15 pm
SYD
-
ORD
3 stops48h 58m
Multiple Airlines
Deal found 3/27$1,106
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:56 pm
ORD
-
SYD
2 stops47h 54m
Multiple Airlines
Tue 5/265:50 pm
SYD
-
ORD
1 stop27h 17m
Multiple Airlines
Deal found 3/27$1,120
This Trip.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
ORD
-
SYD
1 stop32h 35m
Multiple Airlines
Wed 4/299:10 am
SYD
-
ORD
1 stop29h 17m
Multiple Airlines
Deal found 3/24$1,134
This Expedia deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:40 pm
ORD
-
SYD
1 stop24h 40m
Air Canada
Wed 11/1111:20 am
SYD
-
ORD
1 stop20h 21m
Air Canada
Deal found 3/26$1,139
This Air Canada deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:40 pm
ORD
-
SYD
1 stop24h 40m
Air Canada
Wed 10/1410:20 am
SYD
-
ORD
1 stop20h 28m
Air Canada
Deal found 3/26$1,145
This Trip.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Tue 5/59:10 am
SYD
-
MDW
2 stops40h 59m
Multiple Airlines
Deal found 3/23$1,231

Find flight deals from Chicago to Sydney

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sydney (SYD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$971
(Trip.com)

One-way from

$459
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$1,387
Provider with most accurate pricing for Chicago (CHI)-Sydney Kingsford Smith flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Sydney Kingsford Smith flights.
Search Deals
From Chicago (CHI) to Sydney Kingsford Smith
Search Deals
One-way flight from Chicago (CHI) to Sydney Kingsford Smith
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated March 28, 2026.
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

Cheapest round-trip

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 8/15

5:00 pm-6:50 am

2 stops22h 50m

Sydney Kingsford Smith

Sat 8/29

9:15 am-6:39 pm

2 stops24h 24m

$1,612

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 5/16

1:59 pm-6:50 am

2 stops25h 51m

Sydney Kingsford Smith

Tue 5/26

9:15 am-9:09 pm

2 stops26h 54m

$1,612

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/8

1:49 pm-6:50 am

2 stops26h 01m

Sydney Kingsford Smith

Fri 7/10

9:15 am-6:25 pm

2 stops24h 10m

$1,613

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 5/11

1:59 pm-6:50 am

2 stops25h 51m

Sydney Kingsford Smith

Mon 5/18

9:15 am-9:09 pm

2 stops26h 54m

$1,762

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 4/22

12:52 pm-6:50 am

2 stops26h 58m

Sydney Kingsford Smith

Wed 4/29

9:15 am-5:58 pm

2 stops23h 43m

$1,763

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 5/8

1:59 pm-6:50 am

2 stops25h 51m

Sydney Kingsford Smith

Fri 5/15

9:15 am-9:09 pm

2 stops26h 54m

$1,763

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 4/21

12:52 pm-6:50 am

2 stops26h 58m

Sydney Kingsford Smith

Tue 4/28

9:15 am-6:36 pm

2 stops24h 21m

$1,763

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 7/15

6:15 pm-6:50 am

1 stop21h 35m

Sydney Kingsford Smith

Sun 8/9

9:15 am-11:18 pm

1 stop29h 03m

$1,833

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 7/14

2:42 pm-6:50 am

1 stop25h 08m

Sydney Kingsford Smith

Mon 8/10

9:15 am-11:45 pm

1 stop29h 30m

$1,833

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/1

12:53 pm-6:50 am

2 stops26h 57m

Sydney Kingsford Smith

Mon 6/15

9:15 am-6:18 pm

2 stops24h 03m

$1,869

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 45 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Sydney

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Sydney in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Sydney flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sydney flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Sydney flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Sydney flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Sydney flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Sydney

Have a flexible travel schedule? Discover the best time to fly to Sydney from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sydney

How far ahead should I book a flight from Chicago to Sydney?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Sydney. Price data was last updated on March 13, 2026.

The best time to book flights from Chicago to Sydney is 2 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Sydney?

Currently, August is the cheapest month in which you can book a flight from Chicago to Sydney (average of $198). Flying from Chicago to Sydney in October is currently the most expensive (average of $898). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Sydney?

What’s the top layover airport for flights from Chicago to Sydney?

Share of 1-stop round-trip flights from Chicago to Sydney chosen by Cheapflights users in the past 12 months, using the same layover each way.

Los Angeles (LAX) – chosen by Cheapflights users on 29% of 1-stop itineraries from Chicago to Sydney on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Sydney?

Average round-trip fare for 1-stop flights from Chicago to Sydney, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Nadi (NAN) is the most affordable 1-stop option, with an average round-trip price of $845.

What’s the fastest layover option from Chicago to Sydney?

Shortest average travel time for 1-stop one-way flights from Chicago to Sydney, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Los Angeles (LAX) have the shortest average one-way travel time for 1-stop routes: 20h 53m.

Which airport typically offers the quickest layover for flights from Chicago to Sydney?

Average layover duration for 1-stop one-way flights from Chicago to Sydney, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via San Francisco (SFO) offer the fastest connection on this route, with an average layover time of 1h 32m.

Reviews of airlines servicing Sydney

Get insights into the airlines that provide service to Sydney. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sydney. Reviews last updated March 28, 2026.
Peruse reviews from past customers who have flown with ANA,Qantas Airways, andUnited Airlines from Chicago to Sydney to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
ANA
8.4
Very good
1,154 reviews
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
Qantas Airways
7.5
Good
1,013 reviews
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
United Airlines
7.4
Good
9,507 reviews
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
American Airlines
7.1
Good
11,518 reviews
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
Air Canada
7.1
Good
10,856 reviews
ANA
8.4
Very good
1,154 reviews

Comfort

8.2

Boarding

8.5

Entertainment

8.0

Overall

8.4

Food

7.8

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sydney. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Sydney from Chicago?

    Located just 4.6 mi from the city center, Sydney Kingsford Smith is the airport most travelers will use when flying to Sydney from Chicago. Booking flights from Chicago to Kingsford Smith (SYD) should be relatively easy as there are 0 daily inbound flights from Chicago from 7 different airlines.

  • How long is the flight from Chicago to Sydney?

    Delta can get you from Chicago to Sydney in just under 22h 50m. Your travel time can differ by up to . Chicago and Sydney are separated by a distance of 9228 mi.

  • What are the cheapest airlines flying from Chicago to Sydney round-trip?

    Our cheapest airline available from Chicago to Sydney is American Airlines. Our recent data shows that you can find tickets from as low as $198 on this airline. Additional options worth looking into are Fiji Airways and Qantas Airways, starting at $716 and $836 round-trip. These flights start at 85% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Sydney one-way?

    One-way options have recently been found by users for as low as $623 on Qantas Airways. Other airlines that offer cheap prices include ANA from $676 and American Airlines from $817 one-way.

  • Where are the most common layover locations when flying from Chicago to Sydney?

    Chicago to Sydney flights have a layover in Los Angeles most often.

  • What are some popular things to do or see while on a layover in Los Angeles?

    The majority of Los Angeles visitors spend their time at Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live. Travelers on a layover in Los Angeles can visit Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live, by traveling 12.4 mi, 11.7 mi, and 10.9 mi, respectively after landing at Los Angeles Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $44 per day.

  • Where are the least popular layover locations for Chicago to Sydney flights?

    Chicago to Sydney flights have a layover in Dallas least often.

  • Can I find deals for flights from Chicago to Sydney that include hotel bookings?

    Yes. In addition to deals on Chicago to Sydney flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Sydney?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sydney.

  • Can I find deals for business class flights from Chicago to Sydney?

    Yes. Cheapflights offers flight deals from Chicago to Sydney by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Sydney?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Sydney (average of $198). Flying from Chicago to Sydney in October is currently the most expensive (average of $898). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Coogee
Manly

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Sydney

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Sydney flights
St. Louis to Sydney flights

Top 8 airlines flying from Chicago to Sydney

Discover the top 8 airlines that operate flights from Chicago to Sydney. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$1,444FlexibilityNo cancel feeOn-time71%
Fiji AirwaysCheapest$716Average$1,181FlexibilityNo cancel feeOn-time74%
Qantas AirwaysCheapest$836Average$1,362FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$870Average$1,550FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$891Average$1,244FlexibilityNo cancel feeOn-time67%
DeltaCheapest$1,034Average$1,467FlexibilityNo cancel feeOn-timeN/A
ANACheapest$1,177Average$1,259FlexibilityNo cancel feeOn-time80%
Air New ZealandCheapest$1,282Average$1,461FlexibilityNo cancel feeOn-time78%

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