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$498+ Cheap flights from Sydney (SYD) to Chicago (CHI)

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap flight deals from Sydney to Chicago

Cheapest flights from Sydney to Chicago
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 March 28, 2026.

This Trip.com deal was found by Cheapflights users on 3/26. 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 4/251:15 pm
SYD
-
ORD
2 stops31h 20m
Multiple Airlines
Sat 5/23:00 pm
ORD
-
SYD
2 stops29h 50m
Multiple Airlines
Deal found 3/26$906
This BusinessClass deal was found by Cheapflights users on 3/24. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:20 am
SYD
-
ORD
2 stops37h 30m
Multiple Airlines
Thu 6/253:40 pm
ORD
-
SYD
1 stop24h 40m
Multiple Airlines
Deal found 3/24$968
This KAYAK deal was found by Cheapflights users on 3/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:20 am
SYD
-
ORD
2 stops25h 41m
Multiple Airlines
Wed 6/243:40 pm
ORD
-
SYD
1 stop24h 40m
Multiple Airlines
Deal found 3/24$987
This Trip.com deal was found by Cheapflights users on 3/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
SYD
-
ORD
2 stops38h 35m
Multiple Airlines
Fri 5/152:39 pm
ORD
-
SYD
2 stops30h 11m
Multiple Airlines
Deal found 3/24$989
This Air Canada deal was found by Cheapflights users on 3/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:20 am
SYD
-
ORD
1 stop20h 25m
Air Canada
Fri 5/158:45 am
ORD
-
SYD
2 stops31h 35m
Air Canada
Deal found 3/23$1,007
This BusinessClass deal was found by Cheapflights users on 3/24. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:20 am
SYD
-
ORD
1 stop20h 25m
Multiple Airlines
Wed 6/243:40 pm
ORD
-
SYD
1 stop24h 40m
Multiple Airlines
Deal found 3/24$1,039
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Mon 4/205:50 pm
SYD
-
ORD
1 stop20h 37m
Multiple Airlines
Mon 5/42:39 pm
ORD
-
SYD
1 stop25h 51m
Multiple Airlines
Deal found 3/24$1,078
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 4/235:50 pm
SYD
-
ORD
1 stop27h 30m
Multiple Airlines
Wed 5/67:30 am
ORD
-
SYD
1 stop33h 00m
Multiple Airlines
Deal found 3/24$1,095
This Trip.com deal was found by Cheapflights users on 3/28. 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.
Tue 5/121:15 pm
SYD
-
MDW
3 stops36h 54m
Multiple Airlines
Tue 5/196:00 am
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 3/28$1,192
This Trip.com deal was found by Cheapflights users on 3/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:10 am
SYD
-
MDW
2 stops40h 54m
Multiple Airlines
Fri 5/156:00 am
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Deal found 3/24$1,270
This Trip.com deal was found by Cheapflights users on 3/27. 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 5/95:50 pm
SYD
-
MDW
2 stops32h 22m
Multiple Airlines
Sat 5/166:00 am
MDW
-
SYD
2 stops34h 30m
Multiple Airlines
Deal found 3/27$1,379
This Delta deal was found by Cheapflights users on 3/28. 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 5/199:15 am
SYD
-
MDW
2 stops26h 54m
Delta
Tue 5/261:59 pm
MDW
-
SYD
2 stops25h 51m
Delta
Deal found 3/28$1,637

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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$906
(Trip.com)

One-way from

$498
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$1,112
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago (CHI) flights.
Search Deals
From Sydney Kingsford Smith to Chicago (CHI)
Search Deals
One-way flight from Sydney Kingsford Smith to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 2,558,603 searches. Data last updated March 28, 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

Price

Cheapest round-trip

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 5/10

3:40 pm-2:20 pm

2 stops37h 40m

Chicago O'Hare Intl

Sun 5/17

2:00 pm-4:50 pm

1 stop35h 50m

$1,498

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 7/13

11:55 am-10:59 pm

2 stops26h 04m

Chicago O'Hare Intl

Mon 8/10

3:47 pm-8:45 am

2 stops25h 58m

$1,503

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 6/2

9:10 am-7:50 pm

1 stop25h 40m

Chicago O'Hare Intl

Sat 6/27

8:50 pm-7:05 am

1 stop43h 15m

$1,616

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 5/19

9:15 am-9:09 pm

2 stops26h 54m

Chicago Midway

Tue 5/26

1:59 pm-6:50 am

2 stops25h 51m

$1,637

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 6/1

10:20 am-2:50 pm

1 stop19h 30m

Chicago O'Hare Intl

Sat 6/27

9:35 pm-6:55 am

1 stop42h 20m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 5/11

9:15 am-6:33 pm

2 stops24h 18m

Chicago Midway

Mon 5/18

1:22 pm-6:50 am

2 stops26h 28m

$1,644

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 6/3

10:20 am-2:50 pm

1 stop19h 30m

Chicago O'Hare Intl

Sat 6/27

9:35 pm-6:55 am

1 stop42h 20m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 4/20

9:15 am-10:28 pm

2 stops28h 13m

Chicago Midway

Mon 5/4

2:12 pm-6:50 am

2 stops25h 38m

$1,661

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 6/3

9:15 am-5:56 pm

2 stops23h 41m

Chicago Midway

Wed 6/24

1:16 pm-6:50 am

2 stops26h 34m

$1,669
Quickest round-trip

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 6/22

9:10 am-3:52 pm

1 stop21h 42m

Chicago O'Hare Intl

Sun 7/19

7:01 pm-7:05 am

1 stop21h 04m

$1,681

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on 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.
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

How far ahead should I book a flight from Sydney to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Sydney to Chicago. Price data was last updated on March 13, 2026.

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.

What is the cheapest month to book a flight from Sydney to Chicago?

Currently, April is the cheapest month in which you can book a flight from Sydney to Chicago (average of $670). Flying from Sydney to Chicago in January is currently the most expensive (average of $1,315). 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?

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 67% 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 Los Angeles (LAX) have the shortest average one-way travel time for 1-stop routes: 20h 12m.

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 Los Angeles (LAX) offer the fastest connection on this route, with an average layover time of 1h 59m.

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 March 28, 2026.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
1,013 reviews

Food

7.0

Comfort

7.5

Overall

7.5

Crew

8.1

Entertainment

7.2

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Midhat,Feb 2026

WYA - ADL

Frequent delays, 3rd week in a row. Flight attendants not at all friendly.
Qantas Airways
7.5
Good
1,013 reviews
Qantas Airways
7.5
Good
1,013 reviews

Food

7.0

Comfort

7.5

Overall

7.5

Crew

8.1

Entertainment

7.2

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Midhat,Feb 2026

WYA - ADL

Frequent delays, 3rd week in a row. Flight attendants not at all friendly.
United Airlines
7.4
Good
9,503 reviews
Qantas Airways
7.5
Good
1,013 reviews

Food

7.0

Comfort

7.5

Overall

7.5

Crew

8.1

Entertainment

7.2

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Midhat,Feb 2026

WYA - ADL

Frequent delays, 3rd week in a row. Flight attendants not at all friendly.

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.

  • What airport do you fly from for flights from Sydney to Chicago?

    Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago. You should not have trouble finding flights to Chicago from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Sydney airport to Chicago. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.

  • How long is the flight from Sydney to Chicago?

    For as low as $1,644, Air New Zealand can have you in Chicago from Sydney in 19h 30m. The distance from Sydney to Chicago is about 9228 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, United Airlines ($795), and Qantas Airways ($970) offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 31% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Sydney to Chicago one-way?

    The cheapest airlines for a one-way flight from Sydney to Chicago are Air Canada ($530), American Airlines ($772), and Qantas Airways ($796).

  • Can I find deals for flights from Sydney to Chicago that include hotel bookings?

    Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sydney to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.

  • Can I find deals for business class flights from Sydney to Chicago?

    Yes. Cheapflights offers flight deals from Sydney to Chicago 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 Sydney to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Sydney to Chicago (average of $670). Flying from Sydney to Chicago in January is currently the most expensive (average of $1,315). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
Sydney to O'Hare Intl flights
Sydney to St. Louis flights

Top 2 airlines flying from Sydney to Chicago

Discover the top 2 airlines 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 2,558,603 searches. Data last updated March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$795Average$1,279FlexibilityNo cancel feeOn-time69%
Qantas AirwaysCheapest$970Average$1,012FlexibilityNo cancel feeOn-time74%

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