HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$443+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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.

The best prices from Sydney Kingsford Smith to Chicago are usually found in February or March, booked 37 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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$725
(BestPriceTravel)

One-way from

$443
(BestPriceTravel)

Popular in

December

Cheapest in

February

Average price

$857
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. 11% potential increase in price ($141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 22, 2025.

This BestPriceTravel deal was found by Cheapflights users on 2/20. 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/310:10 amSYD - ORD
1 stop25h 33mQantas Airways
Sun 4/208:25 amORD - SYD
1 stop31h 10mQantas Airways
Deal found 2/20$725
This Trip.com deal was found by Cheapflights users on 2/21. 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.
Sat 4/191:45 pmSYD - ORD
2 stops24h 00mMultiple Airlines
Sun 4/278:15 pmORD - SYD
1 stop43h 50mMultiple Airlines
Deal found 2/21$932
This Jettzy deal was found by Cheapflights users on 2/20. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:20 amSYD - ORD
1 stop20h 29mAir Canada
Sun 9/218:25 pmORD - SYD
2 stops43h 55mAir Canada
Deal found 2/20$996
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2811:15 amSYD - ORD
2 stops21h 32mAmerican Airlines
Thu 3/137:17 pmORD - SYD
2 stops25h 08mAmerican Airlines
Deal found 2/21$1,024
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/309:30 amSYD - ORD
1 stop20h 07mUnited Airlines
Sun 5/411:05 amORD - SYD
2 stops28h 50mUnited Airlines
Deal found 2/20$1,097
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/149:25 amSYD - ORD
2 stops24h 24mDelta
Mon 4/286:45 amORD - SYD
2 stops32h 50mDelta
Deal found 2/22$1,111
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/311:05 amSYD - MDW
2 stops24h 06mDelta
Sat 8/161:00 pmMDW - SYD
2 stops26h 35mDelta
Deal found 2/21$1,159
This Aunt Betty deal was found by Cheapflights users on 2/21. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/298:55 amSYD - ORD
2 stops30h 02mJapan Airlines
Sun 9/211:05 amORD - SYD
1 stop38h 15mJapan Airlines
Deal found 2/21$1,271
This BestPriceTravel deal was found by Cheapflights users on 2/21. 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.
Tue 4/111:15 amSYD - ORD
2 stops46h 35mFinnair
Thu 5/89:30 pmORD - SYD
2 stops42h 35mFinnair
Deal found 2/21$1,383
This Gotogate deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/39:55 pmSYD - ORD
2 stops36h 00mTurkish Airlines
Sun 4/2011:25 amORD - SYD
2 stops40h 35mTurkish Airlines
Deal found 2/20$1,511
This Cathay Pacific deal was found by Cheapflights users on 2/21. 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.
Sat 3/2910:20 pmSYD - ORD
1 stop32h 05mCathay Pacific
Mon 4/214:00 pmORD - SYD
1 stop27h 50mCathay Pacific
Deal found 2/21$1,521
This Expedia deal was found by Cheapflights users on 2/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/135:50 pmSYD - ORD
3 stops40h 44mAir Tahiti Nui
Fri 9/266:30 pmORD - SYD
3 stops29h 35mAir Tahiti Nui
Deal found 2/21$1,815

Find flights from Sydney to Chicago within your budget

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 February 22, 2025.

Fly from

Sydney

Fly to

Chicago

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 4/3

10:10 am-7:43 pm

1 stop25h 33m

Chicago O'Hare Intl

Sun 4/20

8:25 am-6:35 am

1 stop31h 10m

$725

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 4/19

1:45 pm-10:45 pm

2 stops24h 00m

Chicago O'Hare Intl

Sun 4/27

8:15 pm-7:05 am

1 stop43h 50m

$932

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 4/17

9:20 am-2:43 pm

1 stop20h 23m

Chicago O'Hare Intl

Wed 4/30

8:52 am-7:20 am

1 stop31h 28m

$1,058

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 4/30

9:30 am-2:37 pm

1 stop20h 07m

Chicago O'Hare Intl

Sun 5/4

11:05 am-6:55 am

2 stops28h 50m

$1,097

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/14

9:25 am-6:49 pm

2 stops24h 24m

Chicago O'Hare Intl

Mon 4/28

6:45 am-6:35 am

2 stops32h 50m

$1,111

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 4/16

9:25 am-6:20 pm

2 stops23h 55m

Chicago Midway

Wed 4/30

1:16 pm-6:35 am

2 stops26h 19m

$1,371

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 4/1

11:15 am-5:50 pm

2 stops46h 35m

Chicago O'Hare Intl

Thu 5/8

9:30 pm-7:05 am

2 stops42h 35m

$1,383

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 4/3

9:55 pm-5:55 pm

2 stops36h 00m

Chicago O'Hare Intl

Sun 4/20

11:25 am-7:00 pm

2 stops40h 35m

$1,511

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 3/29

10:20 pm-2:25 pm

1 stop32h 05m

Chicago O'Hare Intl

Mon 4/21

4:00 pm-10:50 am

1 stop27h 50m

$1,521

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 6/7

8:55 am-7:35 pm

2 stops49h 40m

Chicago O'Hare Intl

Sun 6/22

1:30 am-6:20 am

1 stop37h 50m

$1,702

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 29 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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.

Travel insights for flights from Sydney to Chicago

Get recent, data-driven insights about flights from Sydney to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from Sydney to Chicago is 37 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, August is the cheapest month in which you can book a flight from Sydney to Chicago (average of $245). Flying from Sydney to Chicago in March is currently the most expensive (average of $321). 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 February 22, 2025.

It’s optimal to fly from Sydney to Chicago in the evening. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight in the morning.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 22, 2025.
To help decide which airline to fly from Sydney to Chicago, see what other customers have to say about Air Tahiti Nui, ANA and Korean Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

Air Tahiti Nui
8.7
Very good
61 reviews
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

ANA
8.4
Very good
836 reviews
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

Korean Air
8.4
Very good
1,036 reviews
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

Japan Airlines
8.3
Very good
1,440 reviews
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

Singapore Airlines
8.1
Very good
1,297 reviews
Air Tahiti Nui
8.7
Very good
61 reviews

Food

7.8

Comfort

8.0

Crew

9.1

Boarding

8.7

Entertainment

7.2

Overall

8.7

Reviews

1 / 2

10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

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 3 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.

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

    According to our current data, Qantas Airways ($725), Air Canada ($1,058), and United Airlines ($1,097) offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 35% 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 Qantas Airways ($443), American Airlines ($474), and Cathay Pacific ($866).

  • 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, August is the cheapest month in which you can book a flight from Sydney to Chicago (average of $245). Flying from Sydney to Chicago in March is currently the most expensive (average of $321). 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 Sydney?

Book flights to Sydney if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 3 airlines flying from Sydney to Chicago

Discover the top 3 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$886FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,296FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$964Average$1,593FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.