$695+ Cheap flights from Sydney (SYD) to Chicago (CHI)
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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Find cheap flights from Sydney to Chicago with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Sydney to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Sydney to ChicagoExplore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:00 pm -
3 stops32h 13m
Thu 11/1210:26 am -
3 stops33h 09m
Deal found 9/21![Multiple Airlines logo]()
$1,067
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:05 pm -
2 stops27h 54m
Thu 11/1211:52 am -
2 stops27h 43m
Deal found 9/23![Air New Zealand logo]()
$1,262
This SmartFares deal was found by Cheapflights users on 9/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:20 pm -
1 stop31h 10m
Fri 11/62:10 pm -
1 stop26h 25m
Deal found 9/25![Cathay Pacific logo]()
$1,270
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:20 pm -
1 stop31h 10m
Thu 11/122:10 pm -
1 stop26h 25m
Deal found 9/21![Cathay Pacific logo]()
$1,271
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:20 pm -
1 stop31h 10m
Mon 11/302:10 pm -
1 stop26h 25m
Deal found 9/22![Cathay Pacific logo]()
$1,298
This BestPriceTravel 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:10 am -
1 stop29h 20m
Wed 10/141:50 pm -
1 stop26h 15m
Deal found 9/23![Qantas Airways logo]()
$1,310
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:05 am -
1 stop42h 25m
Wed 11/112:10 pm -
1 stop37h 40m
Deal found 9/20![Cathay Pacific logo]()
$1,318
This BestPriceTravel 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:10 am -
1 stop21h 49m
Tue 10/276:55 pm -
1 stop22h 05m
Deal found 9/21![Qantas Airways logo]()
$1,321
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:10 am -
2 stops30h 19m
Sat 10/246:30 am -
2 stops31h 55m
Deal found 9/20![Multiple Airlines logo]()
$1,325
Best flights from Sydney to ChicagoDiscover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This SmartFares deal was found by Cheapflights users on 9/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:20 pm -
1 stop31h 10m
Fri 11/62:10 pm -
1 stop26h 25m
Deal found 9/25![Cathay Pacific logo]()
$1,270
This BYOjet 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:55 am -
2 stops27h 00m
Thu 10/293:47 pm -
2 stops24h 48m
Deal found 9/24![Air New Zealand logo]()
$1,387
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 11/611:30 am -
2 stops35h 10m
Fri 11/1310:45 pm -
1 stop42h 05m
Deal found 9/22![Multiple Airlines logo]()
$1,425
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:20 pm -
1 stop31h 10m
Mon 11/92:10 pm -
1 stop37h 40m
Deal found 9/24![Cathay Pacific logo]()
$1,326
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:45 pm -
2 stops33h 45m
Thu 11/122:10 pm -
1 stop29h 50m
Deal found 9/21![Multiple Airlines logo]()
$1,452
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/278:45 am -
1 stop44h 45m
Sun 2/282:10 pm -
1 stop48h 05m
Deal found 9/20![Cathay Pacific logo]()
$1,336
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:05 pm -
1 stop38h 50m
Thu 10/293:10 pm -
2 stops39h 20m
Deal found 9/23![Multiple Airlines logo]()
$1,539
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:05 pm -
1 stop38h 50m
Thu 11/52:10 pm -
2 stops33h 20m
Deal found 9/23![Multiple Airlines logo]()
$1,546
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:05 pm -
1 stop38h 50m
Sat 10/244:15 pm -
2 stops47h 50m
Deal found 9/20![Cathay Pacific logo]()
$1,592
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated September 25, 2026 and is based on user searches.
This BestPriceTravel 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:10 am -
1 stop29h 20m
Wed 10/141:50 pm -
1 stop26h 15m
Deal found 9/23![Qantas Airways logo]()
$1,310
This BestPriceTravel 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:10 am -
1 stop21h 49m
Tue 10/276:55 pm -
1 stop22h 05m
Deal found 9/21![Qantas Airways logo]()
$1,321
This BYOjet 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:55 am -
2 stops25h 42m
Thu 10/293:47 pm -
2 stops24h 48m
Deal found 9/23![Air New Zealand logo]()
$1,327
This BestPriceTravel 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:10 am -
1 stop25h 50m
Thu 10/296:55 pm -
1 stop22h 05m
Deal found 9/23![Qantas Airways logo]()
$1,360
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:10 am -
2 stops30h 19m
Sat 10/246:30 am -
2 stops31h 55m
Deal found 9/20![Multiple Airlines logo]()
$1,325
This Cathay Pacific 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1910:20 pm -
1 stop31h 35m
Mon 10/263:10 pm -
1 stop29h 50m
Deal found 9/20![Cathay Pacific logo]()
$1,341
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:50 pm -
1 stop27h 44m
Sat 10/316:30 am -
2 stops31h 55m
Deal found 9/24![Multiple Airlines logo]()
$1,338
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:05 pm -
1 stop38h 25m
Sat 10/313:10 pm -
1 stop29h 50m
Deal found 9/24![Cathay Pacific logo]()
$1,348
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:50 am -
2 stops31h 05m
Sat 10/312:40 pm -
2 stops27h 55m
Deal found 9/24![Air New Zealand logo]()
$1,351
This SmartFares deal was found by Cheapflights users on 9/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:20 pm -
1 stop31h 10m
Fri 11/62:10 pm -
1 stop26h 25m
Deal found 9/25![Cathay Pacific logo]()
$1,270
This BYOjet deal was found by Cheapflights users on 9/25. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:50 am -
2 stops25h 46m
Fri 11/62:00 pm -
2 stops27h 35m
Deal found 9/25![Air New Zealand logo]()
$1,271
One-way flights from Sydney to ChicagoSearch for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Aunt Betty 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:50 pm -
1 stop50h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Etihad Airways logo]()
$695
This BYOjet 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:40 pm -
1 stop39h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Etihad Airways logo]()
$714
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2810:20 pm -
1 stop31h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Cathay Pacific logo]()
$715
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/169:30 pm -
1 stop51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Etihad Airways logo]()
$720
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/99:30 pm -
1 stop51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Etihad Airways logo]()
$721
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:30 pm -
1 stop51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Etihad Airways logo]()
$725
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:30 pm -
1 stop51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Etihad Airways logo]()
$727
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:30 pm -
1 stop51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Etihad Airways logo]()
$730
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/244:50 pm -
1 stop32h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Etihad Airways logo]()
$732
Find flight deals from Sydney to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Chicago (CHI). 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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,067 (Trip.com) |
One-way from | $695 (Aunt Betty) |
Popular in | May |
Cheapest in | October |
Average price | $1,262 |
Cheapflights Fare Finder
Customize your flight search to find flights from Sydney to Chicago 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 25, 2026.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sat 11/7
9:30 pm-7:55 am
1 stop51h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$734
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Tue 12/15
8:20 pm-12:54 am
3 stops45h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$795
Quickest round-trip
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sat 11/7
6:30 pm-12:30 pm
2 stops35h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$903
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 10/1
3:10 pm-1:55 pm
2 stops37h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$938
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Wed 9/30
3:40 pm-2:20 pm
2 stops37h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$990
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 10/29
10:20 pm-1:30 pm
1 stop31h 10m
Chicago O'Hare Intl
Fri 11/6
2:10 pm-9:35 am
1 stop26h 25m
$1,270
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 11/5
10:20 pm-12:30 pm
1 stop31h 10m
Chicago O'Hare Intl
Mon 11/9
2:10 pm-8:50 pm
1 stop37h 40m
$1,326
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Wed 1/27
8:45 am-12:30 pm
1 stop44h 45m
Chicago O'Hare Intl
Sun 2/28
2:10 pm-7:15 am
1 stop48h 05m
$1,336
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Wed 10/14
11:55 am-10:55 pm
2 stops27h 00m
Chicago O'Hare Intl
Thu 10/29
3:47 pm-8:35 am
2 stops24h 48m
$1,387
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Fri 11/6
11:30 am-5:40 am
2 stops35h 10m
Chicago O'Hare Intl
Fri 11/13
10:45 pm-9:50 am
1 stop42h 05m
$1,425
Showing 1-10 of 14 resultsSorted by cheapest first
Compare providers for flights from Sydney to Chicago
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 Sydney to Chicago 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 Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Sydney-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sydney-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sydney-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Sydney-Chicago 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 Sydney-Chicago 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 Sydney to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.
SYD-CHI
SYD-ORD
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 Sydney to Chicago
SYD-CHI
SYD-ORD
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,053). Flying from Sydney to Chicago in May is currently the most expensive (average of $1,432). 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 Sydney to Chicago?
Airfare is typical for this route at the moment.
Sydney to Chicago flights typically cost between $903 and $1,438 in November.The cheapest round-trip price found within the last 5 days was $1,067 on Multiple Airlines (Nov 5-Nov 12).
How far ahead should I book a flight from Sydney to Chicago?
The best time to book flights from Sydney to Chicago is 87 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 Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 25, 2026.
Read through reviews of airlines operating flights from Sydney to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Overall
7.4
Entertainment
7.1
Crew
8.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Overall
7.4
Entertainment
7.1
Crew
8.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Sydney to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
Chicago flight routes
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Other flights from Sydney
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Alternative routes for Sydney to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Sydney to Chicago by cabin class
Find flights from Sydney to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Sydney and Chicago flights
Browse other Sydney and Chicago flight options. Last updated on September 25, 2026.
Other flights from Sydney
Browse through other flights departing from Sydney. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Sydney to Chicago
Discover the top airline that operate flights from Sydney to Chicago. 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$970 | Average$1,633 | FlexibilityNo cancel fee | On-time74% |