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$479+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
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 June 27, 2026.

This Trip.com deal was found by Cheapflights users on 6/23. 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.
Mon 8/246:05 am
MDW
-
SYD
3 stops38h 45m
Multiple Airlines
Tue 9/86:15 am
SYD
-
MDW
3 stops43h 43m
Multiple Airlines
Deal found 6/23$1,069
This Trip.com deal was found by Cheapflights users on 6/23. 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.
Mon 8/249:20 am
ORD
-
SYD
3 stops35h 30m
Multiple Airlines
Tue 9/86:15 am
SYD
-
ORD
2 stops39h 02m
Multiple Airlines
Deal found 6/23$1,073
This lol.travel deal was found by Cheapflights users on 6/26. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:45 pm
ORD
-
SYD
1 stop34h 25m
ANA
Sat 8/2911:45 am
SYD
-
ORD
2 stops32h 00m
ANA
Deal found 6/26$1,195
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:13 pm
ORD
-
SYD
2 stops47h 37m
Multiple Airlines
Wed 8/195:50 pm
SYD
-
ORD
1 stop27h 09m
Multiple Airlines
Deal found 6/26$1,208
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:13 pm
ORD
-
SYD
2 stops47h 37m
Multiple Airlines
Sat 8/295:50 pm
SYD
-
ORD
1 stop27h 27m
Multiple Airlines
Deal found 6/25$1,217
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:13 pm
ORD
-
SYD
2 stops47h 37m
Multiple Airlines
Tue 8/255:50 pm
SYD
-
ORD
1 stop27h 27m
Multiple Airlines
Deal found 6/26$1,231
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:13 pm
ORD
-
SYD
2 stops47h 37m
Multiple Airlines
Sat 8/225:50 pm
SYD
-
ORD
1 stop27h 09m
Multiple Airlines
Deal found 6/26$1,234
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:13 pm
ORD
-
SYD
2 stops58h 12m
Multiple Airlines
Sun 8/235:50 pm
SYD
-
ORD
1 stop27h 09m
Multiple Airlines
Deal found 6/25$1,238
This Rumbo deal was found by Cheapflights users on 6/24. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:45 pm
ORD
-
SYD
1 stop34h 25m
ANA
Sat 8/298:55 pm
SYD
-
ORD
1 stop33h 00m
ANA
Deal found 6/24$1,247
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:46 pm
MDW
-
SYD
2 stops27h 04m
Multiple Airlines
Tue 7/2812:00 pm
SYD
-
MDW
1 stop19h 51m
Multiple Airlines
Deal found 6/23$1,442
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:30 am
MDW
-
SYD
2 stops30h 20m
Delta
Sat 10/2410:15 am
SYD
-
MDW
2 stops22h 35m
Delta
Deal found 6/26$1,610
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:25 pm
MDW
-
SYD
2 stops26h 25m
Delta
Fri 9/49:15 am
SYD
-
MDW
2 stops24h 18m
Delta
Deal found 6/25$1,611

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 June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,069
(Trip.com)

One-way from

$479
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$1,384
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. 7% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 27, 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

Tue 9/1

3:43 pm-6:50 pm

2 stops36h 07m

Sydney Kingsford Smith

Tue 9/8

8:45 pm-6:20 am

3 stops24h 35m

$1,573

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 8/22

1:25 pm-6:50 am

2 stops26h 25m

Sydney Kingsford Smith

Fri 9/4

9:15 am-6:01 pm

2 stops23h 46m

$1,610

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 9/15

1:19 pm-6:50 am

2 stops26h 31m

Sydney Kingsford Smith

Fri 10/2

9:15 am-6:33 pm

2 stops24h 18m

$1,610

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 8/16

6:42 pm-6:50 pm

2 stops33h 08m

Sydney Kingsford Smith

Sat 8/29

8:45 pm-6:20 am

3 stops24h 35m

$1,611

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 9/1

10:54 am-6:50 am

2 stops28h 56m

Sydney Kingsford Smith

Tue 9/8

9:15 am-6:19 pm

2 stops24h 04m

$1,611

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 9/19

11:35 am-6:50 am

2 stops28h 15m

Sydney Kingsford Smith

Sat 9/26

9:15 am-6:20 pm

2 stops24h 05m

$1,611

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 8/13

10:54 am-6:50 am

2 stops28h 56m

Sydney Kingsford Smith

Sat 8/29

9:15 am-6:01 pm

2 stops23h 46m

$1,612

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 7/23

8:20 pm-6:50 pm

2 stops31h 30m

Sydney Kingsford Smith

Fri 8/14

8:45 pm-12:03 pm

2 stops30h 18m

$1,651

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 8/5

12:46 pm-6:50 am

2 stops27h 04m

Sydney Kingsford Smith

Sun 8/30

9:15 am-6:01 pm

2 stops23h 46m

$1,702

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 8/26

6:54 pm-6:50 pm

2 stops32h 56m

Sydney Kingsford Smith

Tue 9/1

8:45 pm-6:20 am

3 stops24h 35m

$1,748

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/26

Showing 1-10 of 37 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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 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

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Sydney (average of $142). Flying from Chicago to Sydney in October is currently the most expensive (average of $831). 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 23% 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: 21h 09m.

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.

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

The best time to book flights from Chicago to Sydney is 46 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.

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 June 27, 2026.
Peruse reviews from past customers who have flown with Delta,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.
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,454 reviews
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Qantas Airways
7.5
Good
1,050 reviews
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
9,898 reviews
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,777 reviews
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Air Canada
7.1
Good
11,269 reviews
Delta
7.8
Good
8,454 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 8 different airlines.

  • How long is the flight from Chicago to Sydney?

    Delta can get you from Chicago to Sydney in just under 26h 25m. Your travel time can differ by up to . Chicago and Sydney are separated by a distance of 9234 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 Delta and Fiji Airways, starting at $261 and $716 round-trip. These flights start at 86% 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 $441 on Qantas Airways. Other airlines that offer cheap prices include ANA from $691 and United Airlines from $836 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 Little Tokyo. Travelers on a layover in Los Angeles can visit Hollywood Bowl, Hollywood Walk of Fame, and Little Tokyo, by traveling 12.4 mi, 11.7 mi, and 12.2 mi, respectively after landing at Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $41 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, May is the cheapest month in which you can book a flight from Chicago to Sydney (average of $142). Flying from Chicago to Sydney in October is currently the most expensive (average of $831). 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 June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$1,443FlexibilityNo cancel feeOn-time71%
DeltaCheapest$261Average$1,547FlexibilityNo cancel feeOn-timeN/A
Fiji AirwaysCheapest$716Average$933FlexibilityNo cancel feeOn-time74%
Qantas AirwaysCheapest$836Average$1,362FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$870Average$1,563FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$898Average$1,267FlexibilityNo cancel feeOn-time67%
ANACheapest$1,193Average$1,288FlexibilityNo cancel feeOn-time80%
Air New ZealandCheapest$1,308Average$1,661FlexibilityNo cancel feeOn-time78%

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