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$527+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sydney Kingsford Smith are usually found in August or May, booked 2 days in advance, depart on a Saturday or Sunday and return on a Thursday

Cheap 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 September 15, 2025.

Round-trip from

$1,033
(Trip.com)

One-way from

$527
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$999
From Chicago (CHI) to Sydney Kingsford Smith
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One-way flight from Chicago (CHI) to Sydney Kingsford Smith
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Highest demand for flights based on searches. 15% potential increase in price ($184 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2712:03 pmMDW - SYD
2 stops28h 57mMultiple Airlines
Sun 11/92:05 pmSYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 9/15$1,033
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:44 amMDW - SYD
2 stops30h 21mMultiple Airlines
Sun 11/22:05 pmSYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 9/15$1,072
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:28 pmORD - SYD
2 stops27h 37mMultiple Airlines
Sun 11/22:05 pmSYD - ORD
2 stops27h 06mMultiple Airlines
Deal found 9/15$1,075
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:05 amORD - SYD
2 stops35h 55mMultiple Airlines
Sun 11/92:05 pmSYD - ORD
2 stops27h 06mMultiple Airlines
Deal found 9/15$1,105
This lol.travel deal was found by Cheapflights users on 9/13. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/34:25 pmORD - SYD
1 stop25h 05mANA
Tue 11/1812:25 pmSYD - ORD
2 stops33h 51mANA
Deal found 9/13$1,161
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/69:48 amORD - SYD
3 stops34h 57mMultiple Airlines
Mon 10/206:00 amSYD - ORD
3 stops34h 17mMultiple Airlines
Deal found 9/15$1,166
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:25 amORD - SYD
2 stops37h 20mMultiple Airlines
Sat 11/12:30 pmSYD - ORD
2 stops24h 30mMultiple Airlines
Deal found 9/15$1,187
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:45 amORD - SYD
3 stops31h 45mMultiple Airlines
Sun 11/162:00 pmSYD - ORD
3 stops33h 25mMultiple Airlines
Deal found 9/15$1,204
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/298:00 amORD - SYD
2 stops31h 25mMultiple Airlines
Sat 11/15:45 pmSYD - ORD
1 stop21h 15mMultiple Airlines
Deal found 9/14$1,205
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/228:00 amORD - SYD
2 stops31h 30mMultiple Airlines
Fri 10/246:45 pmSYD - ORD
1 stop21h 14mMultiple Airlines
Deal found 9/14$1,209
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2910:42 amORD - SYD
2 stops29h 48mMultiple Airlines
Tue 10/710:10 amSYD - ORD
2 stops29h 43mMultiple Airlines
Deal found 9/15$1,210
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:30 amORD - SYD
2 stops38h 30mMultiple Airlines
Thu 11/62:00 pmSYD - ORD
2 stops26h 00mMultiple Airlines
Deal found 9/15$1,213

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 September 15, 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

Mon 11/3

4:25 pm-10:30 am

1 stop25h 05m

Sydney Kingsford Smith

Tue 11/18

12:25 pm-5:16 am

2 stops33h 51m

$1,161

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 11/3

1:49 pm-12:30 pm

2 stops29h 41m

Sydney Kingsford Smith

Tue 11/18

2:10 pm-7:40 pm

2 stops22h 30m

$1,340

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 10/30

7:05 pm-1:00 pm

2 stops25h 55m

Sydney Kingsford Smith

Thu 11/6

2:00 pm-9:24 pm

2 stops24h 24m

$1,368

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 11/6

6:03 pm-1:00 pm

2 stops25h 57m

Sydney Kingsford Smith

Tue 11/11

2:10 pm-7:40 pm

2 stops22h 30m

$1,388

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 9/23

6:30 pm-10:10 pm

2 stops36h 40m

Sydney Kingsford Smith

Thu 10/23

2:15 pm-12:29 am

2 stops26h 14m

$1,404

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 9/20

6:30 pm-10:10 pm

2 stops36h 40m

Sydney Kingsford Smith

Tue 10/21

6:00 am-9:14 pm

2 stops31h 14m

$1,408

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 9/20

6:30 pm-10:10 pm

2 stops36h 40m

Sydney Kingsford Smith

Fri 10/24

6:00 am-12:29 am

2 stops34h 29m

$1,408

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 10/30

6:30 am-9:00 am

2 stops34h 30m

Sydney Kingsford Smith

Thu 11/6

11:20 am-11:30 am

2 stops41h 10m

$1,411

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 11/22

4:57 pm-9:50 pm

2 stops35h 53m

Sydney Kingsford Smith

Tue 12/9

2:10 pm-9:25 pm

2 stops24h 15m

$1,436

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Fri 10/31

3:14 pm-12:30 pm

2 stops29h 16m

Sydney Kingsford Smith

Tue 12/9

2:10 pm-7:19 pm

2 stops22h 09m

$1,436

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
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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 September 12, 2025.

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, March is the cheapest month in which you can book a flight from Chicago to Sydney (average of $1,032). Flying from Chicago to Sydney in December is currently the most expensive (average of $1,627). 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 September 15, 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 14% on your trip compared to booking a flight in the evening.

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 67% 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.

Dallas (DFW) is the most affordable 1-stop option, with an average round-trip price of $889.

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 September 15, 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
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me
ANA
8.4
Very good
961 reviews
ANA
8.4
Very good
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me
Qantas Airways
7.5
Good
905 reviews
ANA
8.4
Very good
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me
United Airlines
7.4
Good
8,929 reviews
ANA
8.4
Very good
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me
American Airlines
7.2
Good
10,000 reviews
ANA
8.4
Very good
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me
Air Canada
7.1
Good
10,000 reviews
ANA
8.4
Very good
961 reviews

Crew

8.7

Comfort

8.2

Overall

8.4

Entertainment

7.9

Boarding

8.6

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me

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?

    ANA, Fiji Airways, and Delta can get you from Chicago to Sydney in just under 25h 05m. Your travel time can differ by up to 11h 35m. 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 $812 and $823 round-trip. These flights start at 30% lower than the current average price 3 months from now.

  • 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 The Wiltern. Travelers on a layover in Los Angeles can visit Hollywood Bowl, Hollywood Walk of Fame, and The Wiltern, by traveling 12.5 mi, 11.7 mi, and 10.0 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, March is the cheapest month in which you can book a flight from Chicago to Sydney (average of $1,032). Flying from Chicago to Sydney in December is currently the most expensive (average of $1,627). 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
O'Hare Intl to Coolangatta flights
Peoria to Sydney 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
ANACheapest$679Average$1,186FlexibilityNo cancel feeOn-time80%
Qantas AirwaysCheapest$812Average$943FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$823Average$870FlexibilityNo cancel feeOn-time71%
DeltaCheapest$846Average$1,034FlexibilityNo cancel feeOn-timeN/A
Fiji AirwaysCheapest$849Average$1,181FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$959Average$1,301FlexibilityNo cancel feeOn-time67%
Air New ZealandCheapest$1,282Average$1,407FlexibilityNo cancel feeOn-time78%
United AirlinesCheapest$1,336Average$1,509FlexibilityNo cancel feeOn-time69%

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