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$589+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or May, booked 82 days in advance, depart on a Thursday or Sunday and return on a Saturday

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$938
(BYOjet)

One-way from

$589
(BYOjet)

Popular in

December

Cheapest in

March

Average price

$1,123
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago (CHI) flights.
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From Sydney Kingsford Smith to Chicago (CHI)
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One-way flight from Sydney Kingsford Smith to Chicago (CHI)
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Highest demand for flights based on searches. 21% potential increase in price ($280 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($46 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This BYOjet deal was found by Cheapflights users on 10/29. 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.
Tue 11/189:55 amSYD - ORD
2 stops26h 35mAir New Zealand
Wed 12/310:38 amORD - SYD
2 stops30h 52mAir New Zealand
Deal found 10/29$938
This BYOjet deal was found by Cheapflights users on 10/30. 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 11/1911:45 amSYD - ORD
2 stops24h 45mAir New Zealand
Thu 12/412:45 pmORD - SYD
2 stops28h 45mAir New Zealand
Deal found 10/30$941
This Trip.com deal was found by Cheapflights users on 10/30. 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.
Wed 11/195:45 pmSYD - ORD
2 stops40h 45mMultiple Airlines
Thu 12/46:50 amORD - SYD
1 stop31h 35mMultiple Airlines
Deal found 10/30$956
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1711:20 amSYD - ORD
1 stop21h 35mAmerican Airlines
Mon 12/11:49 pmORD - SYD
1 stop26h 11mAmerican Airlines
Deal found 10/29$982
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:20 amSYD - ORD
1 stop24h 34mAmerican Airlines
Sun 11/91:49 pmORD - SYD
1 stop26h 11mAmerican Airlines
Deal found 10/30$1,034
This Jetabroad deal was found by Cheapflights users on 10/29. 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.
Tue 11/1811:20 amSYD - ORD
1 stop21h 35mQantas Airways
Wed 12/311:45 amORD - SYD
1 stop28h 15mQantas Airways
Deal found 10/29$1,048
This BestPriceTravel deal was found by Cheapflights users on 10/29. 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.
Tue 11/189:45 pmSYD - ORD
2 stops48h 31mANA
Wed 12/34:25 pmORD - SYD
1 stop34h 50mANA
Deal found 10/29$1,167
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:20 amSYD - ORD
1 stop20h 12mUnited Airlines
Sat 1/247:58 pmORD - SYD
1 stop41h 22mUnited Airlines
Deal found 10/29$1,189
This Booking.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/254:00 pmSYD - ORD
2 stops36h 18mAir Canada
Sat 1/243:40 pmORD - SYD
2 stops48h 05mAir Canada
Deal found 10/29$1,210
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 12/2510:40 amSYD - MDW
2 stops23h 39mDelta
Sat 1/2411:45 amMDW - SYD
2 stops27h 45mDelta
Deal found 10/28$1,407
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/310:40 amSYD - MDW
2 stops22h 34mDelta
Mon 11/171:47 pmMDW - SYD
2 stops25h 43mDelta
Deal found 10/29$1,657
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2310:40 amSYD - MDW
2 stops24h 28mDelta
Sun 11/3010:47 amMDW - SYD
2 stops28h 43mDelta
Deal found 10/27$1,694

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 October 30, 2025.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Fly from

Sydney

Fly to

Chicago

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/19

11:45 am-7:30 pm

2 stops24h 45m

Chicago O'Hare Intl

Thu 12/4

12:45 pm-10:30 am

2 stops28h 45m

$941

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/19

5:45 pm-5:30 pm

2 stops40h 45m

Chicago O'Hare Intl

Thu 12/4

6:50 am-7:25 am

1 stop31h 35m

$956

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 1/20

11:45 am-8:25 pm

2 stops25h 40m

Chicago O'Hare Intl

Sun 1/25

3:53 pm-8:45 am

2 stops23h 52m

$1,025

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 1/23

11:45 am-7:51 pm

2 stops25h 06m

Chicago O'Hare Intl

Sun 2/22

2:33 pm-10:30 am

2 stops26h 57m

$1,028

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 3/29

11:20 am-7:47 am

2 stops36h 27m

Chicago O'Hare Intl

Sat 4/11

9:30 pm-7:00 am

1 stop42h 30m

$1,042

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 3/29

10:20 am-4:36 pm

2 stops46h 16m

Chicago O'Hare Intl

Sat 4/11

3:45 pm-7:20 am

2 stops48h 35m

$1,110

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 11/18

9:45 pm-5:16 am

2 stops48h 31m

Chicago O'Hare Intl

Wed 12/3

4:25 pm-8:15 pm

1 stop34h 50m

$1,167

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 12/25

4:00 pm-11:18 am

2 stops36h 18m

Chicago O'Hare Intl

Sat 1/24

3:40 pm-8:45 am

2 stops48h 05m

$1,210

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 11/17

1:55 pm-7:30 pm

2 stops22h 35m

Chicago O'Hare Intl

Tue 12/2

1:00 pm-8:45 am

2 stops26h 45m

$1,236

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 11/17

11:20 am-8:00 am

2 stops37h 40m

Chicago O'Hare Intl

Mon 12/1

3:40 pm-2:40 pm

2 stops30h 00m

$1,240

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 34 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sydney-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

The best time to book flights from Sydney to Chicago is 82 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, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $620). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,061). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SYD to CHI?

Find hourly flight availability from Sydney to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s optimal to fly from Sydney to Chicago in the afternoon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight at noon.

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.

Los Angeles (LAX) – chosen by Cheapflights users on 86% 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.

Los Angeles (LAX) is the most affordable 1-stop option, with an average round-trip price of $1,065.

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 23m.

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 2h 15m.

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 October 30, 2025.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
925 reviews

Boarding

7.7

Crew

8.2

Overall

7.5

Food

7.0

Comfort

7.5

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
Qantas Airways
7.5
Good
925 reviews
Qantas Airways
7.5
Good
925 reviews

Boarding

7.7

Crew

8.2

Overall

7.5

Food

7.0

Comfort

7.5

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
United Airlines
7.4
Good
8,998 reviews
Qantas Airways
7.5
Good
925 reviews

Boarding

7.7

Crew

8.2

Overall

7.5

Food

7.0

Comfort

7.5

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
American Airlines
7.2
Good
11,030 reviews
Qantas Airways
7.5
Good
925 reviews

Boarding

7.7

Crew

8.2

Overall

7.5

Food

7.0

Comfort

7.5

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.

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 $1,407, Air New Zealand can have you in Chicago from Sydney in 23h 39m. The distance from Sydney to Chicago is about 9234 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, Qantas Airways ($631), and American Airlines ($884) offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 37% less than the average price by searching for these airlines.

  • 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, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $620). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,061). 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
Merrillville
Lansing
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 Midway 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$762FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,129FlexibilityNo cancel feeOn-time71%

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