$471+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Dec 9 — Dec 161
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
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Best
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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 November 9, 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 November 9, 2026.
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Thu 11/122:00 pm -
3 stops27h 21m
Wed 11/257:49 am -
3 stops35h 46m
Deal found 11/6![Multiple Airlines logo]()
$1,148
This lastminute.com deal was found by Cheapflights users on 11/6. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:20 pm -
1 stop31h 10m
Wed 11/252:10 pm -
1 stop26h 25m
Deal found 11/6![Cathay Pacific logo]()
$1,233
This SmartFares deal was found by Cheapflights users on 11/6. 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 11/198:45 am -
1 stop44h 45m
Wed 12/22:10 pm -
1 stop26h 25m
Deal found 11/6![Cathay Pacific logo]()
$1,238
This Air New Zealand deal was found by Cheapflights users on 11/6. 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 Air New Zealand is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:55 am -
2 stops27h 34m
Wed 12/22:29 pm -
2 stops27h 06m
Deal found 11/6![Air New Zealand logo]()
$1,298
This Jettzy deal was found by Cheapflights users on 11/4. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:30 am -
1 stop46h 25m
Fri 12/1110:45 pm -
1 stop42h 05m
Deal found 11/4![Philippine Airlines logo]()
$1,378
This Cathay Pacific deal was found by Cheapflights users on 11/7. 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 11/1611:05 am -
1 stop42h 25m
Thu 12/32:10 pm -
1 stop29h 50m
Deal found 11/7![Cathay Pacific logo]()
$1,428
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Thu 11/1910:20 pm -
1 stop31h 10m
Wed 12/27:00 am -
2 stops30h 25m
Deal found 11/6![Multiple Airlines logo]()
$1,435
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 11/2611:15 am -
2 stops30h 38m
Thu 12/37:00 am -
2 stops30h 25m
Deal found 11/9![Multiple Airlines logo]()
$1,525
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 November 9, 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 November 9, 2026.
This Air New Zealand deal was found by Cheapflights users on 11/6. 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 Air New Zealand is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:55 am -
2 stops27h 34m
Wed 12/22:29 pm -
2 stops27h 06m
Deal found 11/6![Air New Zealand logo]()
$1,298
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 11/266:00 am -
3 stops41h 14m
Thu 12/38:15 pm -
2 stops54h 10m
Deal found 11/9![Multiple Airlines logo]()
$1,558
This Turkish Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 2/49:35 pm -
2 stops37h 45m
Mon 2/88:15 pm -
2 stops54h 10m
Deal found 11/6![Turkish Airlines logo]()
$1,595
This Cathay Pacific deal was found by Cheapflights users on 11/9. 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 4/18:40 am -
1 stop45h 15m
Mon 5/104:15 pm -
2 stops34h 45m
Deal found 11/9![Cathay Pacific logo]()
$1,687
This Qantas Airways deal was found by Cheapflights users on 11/9. 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.
Thu 11/2611:10 am -
1 stop21h 06m
Thu 12/36:49 am -
2 stops31h 06m
Deal found 11/9![Qantas Airways logo]()
$1,713
This Aunt Betty deal was found by Cheapflights users on 11/7. 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 11/269:25 am -
1 stop41h 35m
Fri 12/116:40 am -
2 stops31h 10m
Deal found 11/7![Japan Airlines logo]()
$1,958
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:40 am -
1 stop23h 35m
Mon 1/47:25 am -
1 stop32h 05m
Deal found 11/6![Delta logo]()
$2,075
This Turkish Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 2/189:35 pm -
2 stops37h 45m
Mon 2/228:15 pm -
2 stops54h 10m
Deal found 11/5![Turkish Airlines logo]()
$1,618
This BYOjet deal was found by Cheapflights users on 11/6. 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 11/262:05 pm -
2 stops23h 32m
Fri 12/112:22 pm -
2 stops29h 28m
Deal found 11/6![Air New Zealand logo]()
$1,721
This Qantas Airways deal was found by Cheapflights users on 11/4. 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.
Sun 11/222:05 pm -
2 stops24h 55m
Fri 12/115:15 pm -
1 stop22h 45m
Deal found 11/4![Qantas Airways logo]()
$1,872
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 11/266:20 am -
3 stops40h 54m
Fri 12/116:21 am -
3 stops33h 14m
Deal found 11/9![Multiple Airlines logo]()
$2,022
This Qantas Airways deal was found by Cheapflights users on 11/7. 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.
Sat 12/52:05 pm -
2 stops24h 55m
Sat 12/123:25 pm -
1 stop22h 00m
Deal found 11/7![Qantas Airways logo]()
$2,011
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated November 9, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Thu 11/122:00 pm -
3 stops27h 21m
Wed 11/257:49 am -
3 stops35h 46m
Deal found 11/6![Multiple Airlines logo]()
$1,148
This lastminute.com deal was found by Cheapflights users on 11/6. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:20 pm -
1 stop31h 10m
Wed 11/252:10 pm -
1 stop26h 25m
Deal found 11/6![Cathay Pacific logo]()
$1,233
This Cathay Pacific deal was found by Cheapflights users on 11/7. 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 11/1611:05 am -
1 stop42h 25m
Thu 12/32:10 pm -
1 stop29h 50m
Deal found 11/7![Cathay Pacific logo]()
$1,428
This SmartFares deal was found by Cheapflights users on 11/6. 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 11/198:45 am -
1 stop44h 45m
Wed 12/22:10 pm -
1 stop26h 25m
Deal found 11/6![Cathay Pacific logo]()
$1,238
This Air New Zealand deal was found by Cheapflights users on 11/6. 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 Air New Zealand is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:55 am -
2 stops27h 34m
Wed 12/22:29 pm -
2 stops27h 06m
Deal found 11/6![Air New Zealand logo]()
$1,298
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Thu 11/1910:20 pm -
1 stop31h 10m
Wed 12/27:00 am -
2 stops30h 25m
Deal found 11/6![Multiple Airlines logo]()
$1,435
This Jettzy deal was found by Cheapflights users on 11/4. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:30 am -
1 stop46h 25m
Fri 12/1110:45 pm -
1 stop42h 05m
Deal found 11/4![Philippine Airlines logo]()
$1,378
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 11/2611:15 am -
2 stops30h 38m
Thu 12/37:00 am -
2 stops30h 25m
Deal found 11/9![Multiple Airlines logo]()
$1,525
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 November 9, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Trip.com deal was found by Cheapflights users on 11/4. 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.
Sun 2/286:00 am -
2 stops42h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 3/52:00 pm -
2 stops34h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$521
This Trip.com deal was found by Cheapflights users on 11/8. 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 3/42:00 pm -
2 stops34h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 4/141:15 pm -
3 stops32h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$584
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 3/296:00 pm -
3 stops53h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$660
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 3/202:00 pm -
3 stops32h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$674
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,238 (SmartFares) |
One-way from | $471 (Trip.com) |
Popular in | May |
Cheapest in | October |
Average price | $1,215 |
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 November 9, 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
Fri 3/5
2:00 pm-6:55 pm
3 stops45h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$606
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sat 3/20
2:00 pm-6:10 am
3 stops32h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$674
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sat 3/20
10:20 pm-1:30 pm
1 stop31h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$710
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Mon 3/29
10:30 am-7:05 am
1 stop36h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$827
Quickest round-trip
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 12/3
9:40 pm-5:37 am
3 stops24h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$953
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Fri 12/4
9:40 pm-5:37 am
3 stops24h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$988
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 12/10
9:40 pm-5:37 am
3 stops24h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$1,148
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 11/26
11:15 am-6:14 am
1 stop35h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$1,191
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 12/17
7:35 am-2:30 pm
3 stops47h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-4:00 pm
Nonstop0h 00m
$1,258
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 11/19
11:55 am-10:29 pm
2 stops27h 34m
Chicago O'Hare Intl
Wed 12/2
2:29 pm-10:35 am
2 stops27h 06m
$1,298
Showing 1-10 of 21 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | 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 $1,063). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,589). 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 $795 and $1,402 in January.The cheapest round-trip price found within the last 5 days was $973 on Air Canada (Jan 21-Jan 28).
What’s the top layover airport for flights from Sydney to Chicago?
Share of 1-stop round-trip flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Vancouver (YVR) – chosen by Cheapflights users on 50% of 1-stop itineraries from Sydney to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Sydney to Chicago?
Average round-trip fare for 1-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of $1,323.
What’s the fastest layover option from Sydney to Chicago?
Shortest average travel time for 1-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Vancouver (YVR) have the shortest average one-way travel time for 1-stop routes: 21h 29m.
Which airport typically offers the quickest layover for flights from Sydney to Chicago?
Average layover duration for 1-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Tokyo (HND) offer the fastest connection on this route, with an average layover time of 3h 20m.
How far ahead should I book a flight from Sydney to Chicago?
The best time to book flights from Sydney to Chicago is 81 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 November 9, 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.
Overall
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.7
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 November 9, 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 November 9, 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 November 9, 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$970 | Average$1,633 | FlexibilityNo cancel fee | On-time74% |