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$500+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 87 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 April 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,010
(Mytrip)

One-way from

$500
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$841
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. 16% potential increase in price ($207 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($45 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Mytrip deal was found by Cheapflights users on 4/15. 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.
Fri 5/301:15 pmSYD - ORD
2 stops32h 27mMultiple Airlines
Fri 6/66:59 pmORD - SYD
2 stops25h 46mMultiple Airlines
Deal found 4/15$1,010
This Qantas Airways deal was found by Cheapflights users on 4/14. 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.
Tue 6/245:10 pmSYD - ORD
2 stops37h 34mQantas Airways
Sun 7/68:50 amORD - SYD
2 stops34h 30mQantas Airways
Deal found 4/14$1,079
This Jettzy deal was found by Cheapflights users on 4/14. 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.
Tue 5/2011:50 amSYD - ORD
2 stops32h 14mANA
Thu 8/285:45 pmORD - SYD
1 stop34h 30mANA
Deal found 4/14$1,132
This Flightnetwork deal was found by Cheapflights users on 4/15. 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.
Wed 6/119:20 amSYD - ORD
2 stops43h 41mAir Canada
Sun 12/141:00 pmORD - SYD
2 stops51h 35mAir Canada
Deal found 4/15$1,223
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 6/239:30 amSYD - ORD
2 stops22h 32mUnited Airlines
Mon 7/74:07 pmORD - SYD
2 stops23h 53mUnited Airlines
Deal found 4/14$1,318
This Aunt Betty deal was found by Cheapflights users on 4/14. 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.
Tue 7/810:10 amSYD - ORD
1 stop43h 15mCathay Pacific
Thu 7/174:00 pmORD - SYD
1 stop27h 50mCathay Pacific
Deal found 4/14$1,325
This Delta deal was found by Cheapflights users on 4/14. 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 6/59:25 amSYD - MDW
2 stops24h 20mDelta
Wed 6/1812:44 pmMDW - SYD
2 stops26h 51mDelta
Deal found 4/14$1,327
This Delta deal was found by Cheapflights users on 4/14. 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 7/79:25 amSYD - ORD
2 stops23h 40mDelta
Wed 7/303:35 pmORD - SYD
2 stops24h 00mDelta
Deal found 4/14$1,329
This American Airlines deal was found by Cheapflights users on 4/14. 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 6/239:10 amSYD - ORD
2 stops30h 22mAmerican Airlines
Sat 7/58:40 pmORD - SYD
1 stop43h 25mAmerican Airlines
Deal found 4/14$1,398
This Jetabroad deal was found by Cheapflights users on 4/13. 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 5/298:55 amSYD - ORD
2 stops28h 37mJapan Airlines
Wed 6/41:30 amORD - SYD
1 stop37h 50mJapan Airlines
Deal found 4/13$1,605
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/1210:25 amSYD - MDW
1 stop25h 08mMultiple Airlines
Fri 5/162:45 pmMDW - SYD
1 stop25h 10mMultiple Airlines
Deal found 4/14$2,423
This Korean Air deal was found by Cheapflights users on 4/14. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:55 amSYD - MDW
2 stops43h 40mKorean Air
Mon 5/59:20 amMDW - SYD
2 stops30h 00mKorean Air
Deal found 4/14$5,162

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 April 15, 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

Fri 5/30

1:15 pm-6:42 am

2 stops32h 27m

Chicago O'Hare Intl

Fri 6/6

6:59 pm-11:45 am

2 stops25h 46m

$1,010

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 6/24

5:10 pm-3:44 pm

2 stops37h 34m

Chicago O'Hare Intl

Sun 7/6

8:50 am-10:20 am

2 stops34h 30m

$1,079

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 5/20

11:50 am-5:04 am

2 stops32h 14m

Chicago O'Hare Intl

Thu 8/28

5:45 pm-7:15 pm

1 stop34h 30m

$1,132

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 6/11

9:20 am-2:01 pm

2 stops43h 41m

Chicago O'Hare Intl

Sun 12/14

1:00 pm-9:35 am

2 stops51h 35m

$1,223

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 6/23

9:30 am-5:02 pm

2 stops22h 32m

Chicago O'Hare Intl

Mon 7/7

4:07 pm-7:00 am

2 stops23h 53m

$1,318

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 7/8

10:10 am-2:25 pm

1 stop43h 15m

Chicago O'Hare Intl

Thu 7/17

4:00 pm-10:50 am

1 stop27h 50m

$1,325

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/5

9:25 am-6:45 pm

2 stops24h 20m

Chicago Midway

Wed 6/18

12:44 pm-6:35 am

2 stops26h 51m

$1,327

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 7/7

9:25 am-6:05 pm

2 stops23h 40m

Chicago O'Hare Intl

Wed 7/30

3:35 pm-6:35 am

2 stops24h 00m

$1,329

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 6/23

9:10 am-12:32 am

2 stops30h 22m

Chicago O'Hare Intl

Sat 7/5

8:40 pm-7:05 am

1 stop43h 25m

$1,398

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 5/20

8:55 am-10:32 pm

2 stops28h 37m

Chicago O'Hare Intl

Wed 8/27

1:30 am-6:20 am

1 stop37h 50m

$1,403

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 24 results
1
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 April 11, 2025.

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, 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 April 15, 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 April 15, 2025.
To help decide which airline to fly from Sydney to Chicago, see what other customers have to say about Air Tahiti Nui, Korean Air and Japan Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Tahiti Nui
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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
8.8
Very good
62 reviews
Air Tahiti Nui
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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
1,063 reviews
Air Tahiti Nui
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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
8.3
Very good
841 reviews
Air Tahiti Nui
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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.
Delta
8.0
Very good
7,917 reviews
Air Tahiti Nui
8.8
Very good
62 reviews

Overall

8.8

Comfort

8.1

Entertainment

7.3

Crew

9.1

Food

7.8

Boarding

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 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.

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

    According to our current data, Qantas Airways ($1,079), ANA ($1,132), and Air Canada ($1,223) offers the cheapest pricing from Sydney to Chicago.

  • 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 ($791), Cathay Pacific ($828), and Delta ($839).

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$762FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,296FlexibilityNo cancel feeOn-time71%

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