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$514+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Find cheap flights from Chicago to Sydney with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Sydney Kingsford Smith are usually found in August or June, booked 20 days in advance, depart on a Saturday or Sunday and return on a Thursday

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 December 16, 2025.

This oojo deal was found by Cheapflights users on 12/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:34 pmORD - SYD
1 stop21h 51mQantas Airways
Thu 1/87:15 pmSYD - ORD
2 stops36h 42mQantas Airways
Deal found 12/14$1,131
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/209:04 pmORD - SYD
1 stop41h 21mQantas Airways
Wed 1/75:50 pmSYD - ORD
2 stops38h 07mQantas Airways
Deal found 12/14$1,151
This oojo deal was found by Cheapflights users on 12/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:47 pmORD - SYD
2 stops26h 03mQantas Airways
Fri 12/265:50 pmSYD - ORD
2 stops38h 43mQantas Airways
Deal found 12/14$1,572
This Qantas Airways deal was found by Cheapflights users on 12/13. 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 Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:47 pmORD - SYD
2 stops26h 03mQantas Airways
Sun 1/118:55 amSYD - ORD
2 stops23h 02mQantas Airways
Deal found 12/13$1,589
This Qantas Airways deal was found by Cheapflights users on 12/15. 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 Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:47 pmORD - SYD
2 stops26h 03mQantas Airways
Wed 1/77:15 pmSYD - ORD
2 stops37h 22mQantas Airways
Deal found 12/15$1,611
This Orbitz deal was found by Cheapflights users on 12/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 pmORD - SYD
2 stops46h 35mAir Canada
Wed 1/219:00 amSYD - ORD
2 stops22h 41mAir Canada
Deal found 12/15$1,683
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:00 pmORD - SYD
1 stop22h 00mUnited Airlines
Wed 1/1412:10 pmSYD - ORD
1 stop24h 55mUnited Airlines
Deal found 12/14$1,763
This Delta deal was found by Cheapflights users on 12/15. 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.
Sun 12/2810:00 amORD - SYD
2 stops27h 50mDelta
Sun 1/1110:40 amSYD - ORD
2 stops27h 25mDelta
Deal found 12/15$1,768
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/279:23 pmORD - SYD
1 stop40h 37mUnited Airlines
Sun 1/1111:20 amSYD - ORD
1 stop28h 39mUnited Airlines
Deal found 12/16$1,773
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:23 pmORD - SYD
1 stop40h 37mUnited Airlines
Sun 1/1111:20 amSYD - ORD
2 stops25h 30mUnited Airlines
Deal found 12/13$1,778
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:05 amORD - SYD
1 stop30h 15mUnited Airlines
Fri 1/912:10 pmSYD - ORD
1 stop23h 38mUnited Airlines
Deal found 12/13$1,813
This Delta deal was found by Cheapflights users on 12/15. 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.
Fri 12/266:00 amMDW - SYD
2 stops33h 30mDelta
Wed 1/2110:40 amSYD - MDW
2 stops23h 49mDelta
Deal found 12/15$1,818

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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$901
(lol.travel)

One-way from

$514
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$1,388
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. 16% potential increase in price ($184 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 16, 2025.
Use the filters below to find and compare flights from Chicago to Sydney that are best for you.

Fly from

Chicago

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/17

7:15 am-9:35 am

3 stops33h 20m

Sydney Kingsford Smith

Wed 2/25

11:20 am-8:00 am

2 stops37h 40m

$967

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 3/25

9:15 am-8:35 am

2 stops31h 20m

Sydney Kingsford Smith

Mon 4/6

9:20 am-4:36 pm

2 stops46h 16m

$1,124

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 5/5

7:29 pm-7:05 am

1 stop20h 36m

Sydney Kingsford Smith

Tue 5/19

9:10 am-3:56 pm

1 stop21h 46m

$1,134

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 3/26

4:45 pm-9:00 am

1 stop24h 15m

Sydney Kingsford Smith

Fri 4/10

9:10 am-3:56 pm

1 stop21h 46m

$1,146

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 3/4

6:20 pm-9:05 am

1 stop21h 45m

Sydney Kingsford Smith

Wed 3/18

12:10 pm-5:02 pm

1 stop20h 52m

$1,163

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 5/12

6:20 pm-6:55 am

1 stop21h 35m

Sydney Kingsford Smith

Wed 6/3

10:20 am-2:51 pm

1 stop19h 31m

$1,163

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 1/13

4:16 pm-6:20 am

1 stop21h 04m

Sydney Kingsford Smith

Tue 1/20

11:50 am-5:06 pm

1 stop22h 16m

$1,163

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 3/9

4:35 pm-9:15 am

1 stop24h 40m

Sydney Kingsford Smith

Mon 3/16

12:10 pm-5:02 pm

1 stop20h 52m

$1,163

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/3

4:16 pm-6:20 am

1 stop21h 04m

Sydney Kingsford Smith

Tue 2/17

12:10 pm-2:45 pm

1 stop19h 35m

$1,163

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 2/2

4:16 pm-6:20 am

1 stop21h 04m

Sydney Kingsford Smith

Mon 2/16

12:10 pm-2:45 pm

1 stop19h 35m

$1,163

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 37 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Sydney flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 12, 2025.

The best time to book flights from Chicago to Sydney is 20 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 December is currently the most expensive (average of $851). 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.

What is the cheapest time of day to fly from CHI to SYD?

Find hourly flight availability from Chicago to Sydney. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Sydney in the morning. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Chicago to Sydney?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sydney. Price data was last updated on December 8, 2024.

Travelers seeking maximum savings on their Chicago to Sydney flight should consider departing on Sunday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 43% 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.

San Francisco (SFO) is the most affordable 1-stop option, with an average round-trip price of $870.

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 Dallas (DFW) have the shortest average one-way travel time for 1-stop routes: 21h 02m.

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 Dallas (DFW) 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 December 16, 2025.
Peruse reviews from past customers who have flown with ANA, Qantas Airways, and United 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
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support
ANA
8.4
Very good
1,025 reviews
ANA
8.4
Very good
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support
Qantas Airways
7.5
Good
946 reviews
ANA
8.4
Very good
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support
United Airlines
7.4
Good
9,092 reviews
ANA
8.4
Very good
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support
American Airlines
7.2
Good
11,049 reviews
ANA
8.4
Very good
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support
Air Canada
7.1
Good
10,531 reviews
ANA
8.4
Very good
1,025 reviews

Comfort

8.2

Food

7.7

Overall

8.4

Boarding

8.6

Crew

8.7

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mario,Nov 2025

HND - BKK

Option to use Bluetooth headphones when connecting to in flight entertainment system. I want to use my own headsets with noise cancelling support

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?

    Air Canada, Qantas Airways, and United Airlines can get you from Chicago to Sydney in just under 20h 36m. Your travel time can differ by up to 12h 44m. Chicago and Sydney are separated by a distance of 9228 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Our cheapest airline available from Chicago to Sydney is ANA. Our recent data shows that you can find tickets from as low as $679 on this airline. Additional options worth looking into are Qantas Airways and American Airlines, starting at $802 and $814 round-trip. These flights start at 28% 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 $304 on ANA. Other airlines that offer cheap prices include Qantas Airways from $396 and American Airlines from $409 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 12.5 mi, 11.7 mi, and 10.8 mi, respectively after landing at Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $37 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 December is currently the most expensive (average of $851). 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
Manly
Coogee

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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
Midway to Sydney flights
St. Louis to Sydney flights
Peoria to Sydney flights
O'Hare Intl to Coolangatta flights
Evansville 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
ANACheapest$679Average$1,209FlexibilityNo cancel feeOn-time80%
Qantas AirwaysCheapest$810Average$896FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$814Average$851FlexibilityNo cancel feeOn-time71%
Fiji AirwaysCheapest$849Average$1,181FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$851Average$1,215FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$870Average$1,540FlexibilityNo cancel feeOn-time69%
DeltaCheapest$935Average$1,034FlexibilityNo cancel feeOn-timeN/A
Air New ZealandCheapest$1,282Average$1,501FlexibilityNo cancel feeOn-time78%

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