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$478+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 24 days in advance, depart on a Thursday or Sunday and return on a Tuesday

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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

March

Round-trip from

$1,044
(BestPriceTravel)

One-way from

$478
(Kiwi.com)
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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High demand for flights, 22% potential price rise
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Best time to find cheap flights, 13% potential price drop
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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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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 November 21, 2024.

This ANA deal was found by Cheapflights users on 11/20. 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 ANA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2512:25 pmSYD - ORD
2 stops33h 36mANA
Tue 12/104:25 pmORD - SYD
1 stop25h 05mANA
Deal found 11/20$1,174
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:00 amSYD - ORD
3 stops40h 30mMultiple Airlines
Mon 1/68:52 amORD - SYD
2 stops34h 38mMultiple Airlines
Deal found 11/20$1,232
This BestPriceTravel deal was found by Cheapflights users on 11/20. 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.
Wed 12/411:15 amSYD - ORD
1 stop21h 37mQantas Airways
Sun 12/83:23 pmORD - SYD
1 stop24h 37mQantas Airways
Deal found 11/20$1,315
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:15 amSYD - ORD
1 stop23h 14mAmerican Airlines
Sun 1/52:58 pmORD - SYD
1 stop23h 27mAmerican Airlines
Deal found 11/20$1,321
This Air Canada deal was found by Cheapflights users on 11/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/411:20 amSYD - ORD
2 stops37h 36mAir Canada
Sun 12/811:35 amORD - SYD
2 stops29h 00mAir Canada
Deal found 11/20$1,327
This United Airlines deal was found by Cheapflights users on 11/19. 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 11/2511:20 amSYD - ORD
2 stops22h 35mUnited Airlines
Sat 1/46:25 pmORD - SYD
1 stop21h 40mUnited Airlines
Deal found 11/19$1,667
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/411:05 amSYD - MDW
2 stops24h 27mDelta
Sun 12/89:30 amMDW - SYD
2 stops30h 05mDelta
Deal found 11/20$1,809
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2611:05 amSYD - ORD
2 stops28h 09mDelta
Thu 12/128:35 amORD - SYD
2 stops31h 00mDelta
Deal found 11/20$1,859
This KAYAK deal was found by Cheapflights users on 11/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/168:10 amSYD - ORD
3 stops38h 57mChina Southern
Thu 1/212:45 pmORD - SYD
3 stops48h 50mChina Southern
Deal found 11/21$2,631
This Bravofly deal was found by Cheapflights users on 11/20. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/268:55 amSYD - ORD
3 stops27h 49mAir Tahiti Nui
Sun 1/55:10 pmORD - SYD
3 stops31h 30mAir Tahiti Nui
Deal found 11/20$2,697
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/209:40 pmSYD - MDW
2 stops43h 47mMultiple Airlines
Fri 12/272:15 pmMDW - SYD
1 stop23h 20mMultiple Airlines
Deal found 11/20$3,340

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 3/10

5:25 pm-11:34 pm

1 stop22h 09m

Chicago O'Hare Intl

Mon 4/7

3:00 pm-7:05 am

1 stop25h 05m

$1,044

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/23

6:15 am-12:40 am

2 stops35h 25m

Chicago O'Hare Intl

Thu 1/30

11:10 am-1:00 pm

2 stops32h 50m

$1,059

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 3/10

11:20 am-2:51 pm

2 stops43h 31m

Chicago O'Hare Intl

Mon 4/7

1:00 pm-7:20 am

2 stops27h 20m

$1,083

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/4

9:45 pm-7:20 am

1 stop26h 35m

Chicago O'Hare Intl

Sun 12/8

7:15 am-8:15 pm

2 stops44h 00m

$1,195

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 5/16

5:35 pm-6:00 am

1 stop27h 25m

Chicago O'Hare Intl

Fri 5/23

10:00 am-6:35 am

1 stop29h 35m

$1,229

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 1/23

11:05 am-5:47 pm

2 stops23h 42m

Chicago Midway

Tue 2/25

2:08 pm-8:35 am

2 stops25h 27m

$1,344

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 5/16

10:20 am-6:54 pm

2 stops23h 34m

Chicago O'Hare Intl

Fri 5/23

2:18 pm-7:00 am

2 stops25h 42m

$1,432

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 3/9

8:55 am-10:34 pm

3 stops30h 39m

Chicago O'Hare Intl

Sun 4/6

6:45 pm-3:05 pm

3 stops29h 20m

$1,707

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 1/23

11:50 am-8:53 pm

1 stop26h 03m

Chicago Midway

Thu 1/30

2:56 pm-6:35 am

1 stop22h 39m

$2,181

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 12/25

11:05 am-10:52 pm

2 stops28h 47m

Chicago O'Hare Intl

Sun 1/5

10:45 am-6:50 am

2 stops27h 05m

$2,516

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 29 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust 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.

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 November 15, 2024.

The best time to book flights from Sydney to Chicago is 24 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 $232). Flying from Sydney to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

It’s optimal to fly from Sydney to Chicago at noon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the evening.

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 November 21, 2024.
To help decide which airline to fly from Sydney to Chicago, see what other customers have to say about Qantas Airways, Air Canada and ANA. 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
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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
68 reviews
Air Tahiti Nui
8.7
Very good
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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
8.5
Very good
1,025 reviews
Air Tahiti Nui
8.7
Very good
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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
833 reviews
Air Tahiti Nui
8.7
Very good
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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
1,460 reviews
Air Tahiti Nui
8.7
Very good
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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
8,758 reviews
Air Tahiti Nui
8.7
Very good
68 reviews

Boarding

8.5

Comfort

8.0

Entertainment

7.2

Food

7.7

Overall

8.7

Crew

9.0

Reviews

1 / 2

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 ($1,044), Air Canada ($1,083), and ANA ($1,195) offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 15% 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 ($518), American Airlines ($550), and United Airlines ($849).

  • 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 $232). Flying from Sydney to Chicago in June is currently the most expensive (average of $308). 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

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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 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$892Average$1,239FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$964Average$1,593FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$986Average$1,282FlexibilityNo cancel feeOn-time67%
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