$516+ Cheap flights from Chicago (CHI) to Sydney (SYD)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Sydney
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Cheapest flights from Chicago to SydneyExplore 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 24, 2026.
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 24, 2026.
This oojo deal was found by Cheapflights users on 9/20. 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 11/27:29 am -
2 stops34h 06m
Mon 11/169:55 am -
2 stops29h 05m
Deal found 9/20![Air New Zealand logo]()
$1,235
This oojo deal was found by Cheapflights users on 9/19. 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 11/89:21 am -
2 stops30h 14m
Wed 11/1811:50 am -
2 stops24h 06m
Deal found 9/19![Air New Zealand logo]()
$1,239
This FlightHub deal was found by Cheapflights users on 9/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:55 pm -
2 stops43h 40m
Wed 11/259:55 am -
2 stops30h 32m
Deal found 9/20![Air New Zealand logo]()
$1,244
This oojo deal was found by Cheapflights users on 9/20. 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 11/19:21 am -
2 stops30h 14m
Sun 11/157:25 pm -
2 stops42h 12m
Deal found 9/20![Air New Zealand logo]()
$1,258
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 11/104:25 pm -
1 stop34h 50m
Tue 11/1712:25 pm -
2 stops33h 55m
Deal found 9/22![ANA logo]()
$1,260
This lol.travel deal was found by Cheapflights users on 9/21. 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 10/183:40 pm -
1 stop24h 40m
Sun 11/111:20 am -
1 stop25h 39m
Deal found 9/21![Air Canada logo]()
$1,262
This Mytrip deal was found by Cheapflights users on 9/20. 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.
Tue 10/206:30 am -
2 stops33h 00m
Tue 10/2711:15 am -
2 stops29h 06m
Deal found 9/20![Multiple Airlines logo]()
$1,267
This Gotogate deal was found by Cheapflights users on 9/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:30 am -
1 stop40h 45m
Tue 11/2412:25 pm -
1 stop35h 55m
Deal found 9/20![ANA logo]()
$1,274
This SmartFares deal was found by Cheapflights users on 9/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:25 pm -
1 stop34h 50m
Tue 11/2412:25 pm -
1 stop35h 55m
Deal found 9/20![ANA logo]()
$1,276
Best flights from Chicago to SydneyDiscover carefully curated flight deals from Chicago to Sydney that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Chicago to Sydney that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This Philippine Airlines deal was found by Cheapflights users on 9/22. 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 Philippine Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/56:59 am -
2 stops33h 51m
Tue 3/1611:30 am -
1 stop46h 25m
Deal found 9/22![Multiple Airlines logo]()
$1,291
This Qantas Airways deal was found by Cheapflights users on 9/22. 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.
Tue 12/295:59 pm -
1 stop22h 01m
Thu 1/212:05 pm -
1 stop22h 54m
Deal found 9/22![Qantas Airways logo]()
$1,644
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/167:35 am -
1 stop31h 55m
Sat 1/2310:40 am -
1 stop23h 41m
Deal found 9/23![Delta logo]()
$1,674
This Turkish Airlines deal was found by Cheapflights users on 9/23. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1511:45 am -
2 stops38h 40m
Sun 11/299:35 pm -
2 stops53h 25m
Deal found 9/23![Turkish Airlines logo]()
$1,737
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/138:00 am -
3 stops29h 25m
Wed 2/39:25 pm -
3 stops32h 48m
Deal found 9/19![Alaska Airlines logo]()
$2,557
This KLM deal was found by Cheapflights users on 9/23. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:25 pm -
3 stops46h 00m
Sun 11/2911:10 am -
3 stops44h 15m
Deal found 9/23![KLM logo]()
$2,826
This Emirates deal was found by Cheapflights users on 9/19. 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 Emirates is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:45 pm -
2 stops42h 50m
Tue 11/1010:25 am -
2 stops45h 30m
Deal found 9/19![Emirates logo]()
$2,873
This Delta deal was found by Cheapflights users on 9/22. 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 10/109:30 am -
1 stop30h 20m
Sat 10/1710:15 am -
1 stop21h 30m
Deal found 9/22![Delta logo]()
$1,713
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/298:59 pm -
2 stops29h 46m
Thu 1/219:40 pm -
3 stops32h 33m
Deal found 9/23![Multiple Airlines logo]()
$1,735
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/298:59 pm -
2 stops29h 46m
Sat 1/239:40 pm -
3 stops32h 33m
Deal found 9/19![Multiple Airlines logo]()
$1,749
This Alaska Airlines deal was found by Cheapflights users on 9/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:49 pm -
2 stops35h 01m
Fri 10/168:45 pm -
3 stops24h 55m
Deal found 9/21![Multiple Airlines logo]()
$1,756
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:57 pm -
3 stops31h 48m
Thu 2/49:40 pm -
2 stops32h 35m
Deal found 9/23![Multiple Airlines logo]()
$2,280
Last-minute flights from Chicago to SydneyDiscover last-minute flight deals from Chicago to Sydney. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sydney. Data last updated September 24, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 9/21. 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 10/183:40 pm -
1 stop24h 40m
Sun 11/111:20 am -
1 stop25h 39m
Deal found 9/21![Air Canada logo]()
$1,262
This Philippine Airlines deal was found by Cheapflights users on 9/24. 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 Philippine Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops35h 00m
Sun 11/111:30 am -
2 stops34h 32m
Deal found 9/24![Multiple Airlines logo]()
$1,310
This Flightnetwork deal was found by Cheapflights users on 9/23. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:40 pm -
1 stop24h 40m
Sun 11/111:20 am -
2 stops25h 32m
Deal found 9/23![Air Canada logo]()
$1,312
This Mytrip deal was found by Cheapflights users on 9/20. 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.
Tue 10/206:30 am -
2 stops33h 00m
Tue 10/2711:15 am -
2 stops29h 06m
Deal found 9/20![Multiple Airlines logo]()
$1,267
This lol.travel deal was found by Cheapflights users on 9/20. 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.
Wed 10/213:40 pm -
1 stop24h 40m
Wed 10/2810:20 am -
1 stop20h 17m
Deal found 9/20![Air Canada logo]()
$1,301
This Justfly.com deal was found by Cheapflights users on 9/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:00 pm -
2 stops25h 35m
Wed 11/42:05 pm -
2 stops24h 57m
Deal found 9/19![Air New Zealand logo]()
$1,283
This FlightHub deal was found by Cheapflights users on 9/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:00 pm -
2 stops43h 35m
Sat 10/3111:50 am -
2 stops24h 47m
Deal found 9/24![Air New Zealand logo]()
$1,295
This lol.travel deal was found by Cheapflights users on 9/22. 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 10/253:30 pm -
1 stop25h 05m
Sun 11/811:20 am -
2 stops25h 32m
Deal found 9/22![Air Canada logo]()
$1,314
One-way flights from Chicago to SydneySearch for one-way flight options from Chicago to Sydney. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Chicago to Sydney. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/208:01 pm -
1 stop43h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/248:01 pm -
1 stop42h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$517
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Wed 10/218:01 pm -
1 stop43h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 11/176:30 am -
2 stops30h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$559
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Fri 10/238:01 pm -
1 stop42h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Sat 12/57:25 am -
2 stops30h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Sat 11/76:30 am -
2 stops54h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$575
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/228:01 pm -
1 stop42h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/196:30 am -
2 stops57h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$584
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 September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,235 (oojo) |
One-way from | $516 (Kiwi.com) |
Popular in | December |
Cheapest in | June |
Average price | $1,605 |
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 7,457,451 searches. Data last updated September 24, 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
Cheapest round-trip
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Thu 3/4
6:59 am-9:50 am
2 stops33h 51m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$622
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Thu 3/18
6:59 am-9:50 am
2 stops34h 51m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$622
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 3/7
8:45 pm-9:50 am
2 stops44h 05m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$622
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 10/25
6:00 am-9:50 am
2 stops35h 50m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$686
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sat 10/31
8:30 pm-9:50 am
2 stops45h 20m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$687
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Thu 11/19
5:40 am-9:50 am
2 stops35h 10m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$687
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Fri 10/2
6:00 am-8:00 am
2 stops35h 00m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$726
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sun 11/1
2:10 pm-10:45 am
3 stops51h 35m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$730
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Sat 10/10
8:01 pm-7:30 am
1 stop43h 29m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$785
Quickest round-trip
ChicagoSydney
ORD Chicago O'Hare Intl - SYD Sydney Kingsford Smith
ORDSYD
Chicago O'Hare Intl
Tue 11/10
7:20 am-6:25 am
3 stops30h 05m
Sydney Kingsford Smith
Wed 12/31
12:00 am-8:00 am
Nonstop0h 00m
$836
Showing 1-10 of 23 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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.
CHI-SYD
ORD-SYD
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
CHI-SYD
ORD-SYD
What is the cheapest month to book a flight from Chicago to Sydney?
Currently, February is the cheapest month in which you can book a flight from Chicago to Sydney (average of $1,244). Flying from Chicago to Sydney in December is currently the most expensive (average of $1,758). 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?
Airfare is below average for this route at the moment.
Chicago to Sydney flights typically cost between $1,259 and $1,788 in November.The cheapest round-trip price found within the last 5 days was $1,235 on Air New Zealand (Nov 2-Nov 16).
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 57% 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 11m.
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 83 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 September 24, 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.
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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.
Traveling to a place near Sydney?
Book flights to Sydney if you plan to visit one of these locationsParramatta
Wollongong
Coogee
Manly
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Chicago and Sydney flights
Browse other Chicago and Sydney flight options. Last updated on September 24, 2026.
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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 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$237 | Average$1,530 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$716 | Average$819 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$837 | Average$1,364 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$837 | Average$1,545 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$870 | Average$1,590 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$1,117 | Average$1,312 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$1,193 | Average$1,270 | FlexibilityNo cancel fee | On-time80% | |
| Cheapest$1,294 | Average$1,662 | FlexibilityNo cancel fee | On-time78% |