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$388+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in February 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 July 31, 2025.

Round-trip from

$1,050
(Qantas Airways)

One-way from

$388
(flugladen.de)

Popular in

December

Cheapest in

February

Average price

$1,047
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. 18% potential increase in price ($236 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Qantas Airways deal was found by Cheapflights users on 7/30. 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 Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/49:10 amSYD - ORD
1 stop20h 07mQantas Airways
Mon 8/257:03 pmORD - SYD
1 stop21h 27mQantas Airways
Deal found 7/30$1,047
This BYOjet deal was found by Cheapflights users on 7/29. 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.
Sat 9/279:20 amSYD - ORD
1 stop25h 44mAir Canada
Tue 10/148:51 amORD - SYD
1 stop31h 29mAir Canada
Deal found 7/29$1,054
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/49:10 amSYD - ORD
2 stops23h 10mAmerican Airlines
Mon 8/254:21 pmORD - SYD
2 stops26h 19mAmerican Airlines
Deal found 7/30$1,055
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:15 pmSYD - ORD
3 stops30h 34mMultiple Airlines
Fri 9/1911:48 amORD - SYD
3 stops32h 57mMultiple Airlines
Deal found 7/29$1,072
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 9/69:30 amSYD - ORD
2 stops23h 56mUnited Airlines
Sun 10/57:10 amORD - SYD
1 stop32h 50mUnited Airlines
Deal found 7/29$1,073
This Air New Zealand deal was found by Cheapflights users on 7/30. 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 Air New Zealand is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/511:50 amSYD - ORD
2 stops26h 09mAir New Zealand
Tue 8/264:10 pmORD - SYD
2 stops25h 35mAir New Zealand
Deal found 7/30$1,147
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:40 pmSYD - ORD
2 stops30h 31mAlaska Airlines
Tue 10/710:05 amORD - SYD
2 stops41h 40mAlaska Airlines
Deal found 7/29$1,186
This Delta deal was found by Cheapflights users on 7/31. 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 10/299:40 amSYD - MDW
2 stops24h 45mDelta
Sat 11/151:00 pmMDW - SYD
2 stops26h 30mDelta
Deal found 7/31$1,392
This Korean Air deal was found by Cheapflights users on 7/31. 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.
Sun 8/317:55 amSYD - MDW
2 stops43h 33mMultiple Airlines
Thu 9/119:35 amMDW - SYD
2 stops29h 45mMultiple Airlines
Deal found 7/31$11,188

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 July 31, 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

Mon 8/11

9:10 am-3:55 pm

1 stop21h 45m

Chicago O'Hare Intl

Wed 9/3

7:01 pm-7:05 am

1 stop21h 04m

$1,050

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 9/27

9:20 am-8:04 pm

1 stop25h 44m

Chicago O'Hare Intl

Tue 10/14

8:51 am-8:20 am

1 stop31h 29m

$1,054

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 9/6

9:10 am-9:22 pm

1 stop27h 12m

Chicago O'Hare Intl

Mon 10/6

10:10 am-8:05 am

1 stop29h 55m

$1,056

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/12

1:15 pm-4:49 am

3 stops30h 34m

Chicago O'Hare Intl

Fri 9/19

11:48 am-11:45 am

3 stops32h 57m

$1,072

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 9/6

9:30 am-2:35 pm

1 stop20h 05m

Chicago O'Hare Intl

Sat 10/4

9:13 pm-7:55 am

1 stop42h 42m

$1,073

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/12

9:40 pm-1:11 pm

2 stops30h 31m

Chicago O'Hare Intl

Tue 10/7

10:05 am-7:45 pm

2 stops41h 40m

$1,186

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/12

10:40 am-6:34 pm

2 stops24h 54m

Chicago Midway

Sun 2/1

1:00 pm-8:30 am

2 stops26h 30m

$1,350

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 8/31

7:55 am-12:28 pm

2 stops43h 33m

Chicago Midway

Thu 9/11

9:35 am-6:20 am

2 stops29h 45m

$11,188

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/15

5:20 pm-5:01 am

2 stops27h 41m

$388

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 10/9

9:30 pm-8:45 am

1 stop51h 15m

$642

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 17 results
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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 July 25, 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, 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 July 31, 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.

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 July 31, 2025.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Korean Air, Alaska Airlines, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
Korean Air
8.4
Very good
1,121 reviews
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
Alaska Airlines
8.0
Very good
10,000 reviews
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
Delta
8.0
Very good
7,981 reviews
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
Cathay Pacific
7.6
Good
949 reviews
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.
Qantas Airways
7.5
Good
887 reviews
Korean Air
8.4
Very good
1,121 reviews

Overall

8.4

Comfort

8.2

Crew

8.7

Boarding

8.5

Food

8.1

Entertainment

8.2

Reviews

1 / 20
10.0
Excellent

Myung Suk,May 2025

ICN - LAX

The flight was less crowded and the economic class seat was at least 5 inches longer than other airlines.

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 ($1,050), Air Canada ($1,054), and American Airlines ($1,056) 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 Etihad Airways ($642), American Airlines ($691), and Air Canada ($828).

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 Midway flights
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$762FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,296FlexibilityNo cancel feeOn-time71%

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