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$499+ 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
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 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 June 12, 2025.

Round-trip from

$1,046
(Trip.com)

One-way from

$499
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$1,087
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. 19% potential increase in price ($250 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($51 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Trip.com deal was found by Cheapflights users on 6/12. 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.
Thu 8/141:15 pmSYD - ORD
2 stops24h 31mMultiple Airlines
Thu 9/46:20 amORD - SYD
2 stops38h 55mMultiple Airlines
Deal found 6/12$1,046
This Delta deal was found by Cheapflights users on 6/12. 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 7/219:25 amSYD - MDW
2 stops23h 14mDelta
Mon 8/1812:43 pmMDW - SYD
2 stops26h 52mDelta
Deal found 6/12$1,093
This Delta deal was found by Cheapflights users on 6/12. 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 7/219:25 amSYD - ORD
2 stops22h 25mDelta
Wed 8/202:15 pmORD - SYD
2 stops25h 20mDelta
Deal found 6/12$1,093
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/138:55 pmSYD - ORD
1 stop26h 45mANA
Thu 7/319:05 amORD - SYD
2 stops43h 10mANA
Deal found 6/12$1,098
This American Airlines deal was found by Cheapflights users on 6/12. 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
1 stop23h 32mAmerican Airlines
Mon 8/256:00 amORD - SYD
1 stop34h 05mAmerican Airlines
Deal found 6/12$1,129
This Aunt Betty deal was found by Cheapflights users on 6/12. 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.
Wed 7/238:55 amSYD - ORD
2 stops29h 48mJapan Airlines
Tue 8/191:30 amORD - SYD
1 stop37h 50mJapan Airlines
Deal found 6/12$1,217
This Flighttix deal was found by Cheapflights users on 6/9. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/179:10 amSYD - ORD
1 stop21h 34mBritish Airways
Mon 7/2810:17 pmORD - SYD
1 stop41h 48mBritish Airways
Deal found 6/9$1,232
This Gotogate deal was found by Cheapflights users on 6/10. 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.
Wed 10/810:20 amSYD - ORD
2 stops27h 47mAir Canada
Thu 10/168:55 amORD - SYD
2 stops31h 25mAir Canada
Deal found 6/10$1,275
This lastminute.com deal was found by Cheapflights users on 6/11. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/127:40 amSYD - ORD
1 stop45h 45mCathay Pacific
Wed 6/254:00 pmORD - SYD
1 stop27h 50mCathay Pacific
Deal found 6/11$1,374
This United Airlines deal was found by Cheapflights users on 6/10. 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 stop26h 02mUnited Airlines
Fri 1/2312:45 pmORD - SYD
1 stop24h 35mUnited Airlines
Deal found 6/10$1,410
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/199:40 pmSYD - ORD
2 stops47h 00mAlaska Airlines
Wed 7/306:00 amORD - SYD
2 stops46h 45mAlaska Airlines
Deal found 6/11$1,462
This WestJet deal was found by Cheapflights users on 6/12. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/198:30 pmSYD - MDW
2 stops28h 15mWestJet
Mon 7/289:24 amMDW - SYD
2 stops30h 11mWestJet
Deal found 6/12$7,672

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 June 12, 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

Thu 8/14

1:15 pm-10:46 pm

2 stops24h 31m

Chicago O'Hare Intl

Thu 9/4

6:20 am-12:15 pm

2 stops38h 55m

$1,046

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 7/21

9:25 am-5:39 pm

2 stops23h 14m

Chicago Midway

Mon 8/18

12:43 pm-6:35 am

2 stops26h 52m

$1,093

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 7/21

9:25 am-4:50 pm

2 stops22h 25m

Chicago O'Hare Intl

Wed 8/20

2:15 pm-6:35 am

2 stops25h 20m

$1,093

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 8/4

8:55 pm-8:40 am

1 stop26h 45m

Chicago O'Hare Intl

Mon 8/25

8:20 pm-7:15 pm

2 stops31h 55m

$1,115

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 8/4

9:10 am-5:42 pm

1 stop23h 32m

Chicago O'Hare Intl

Mon 8/25

6:00 am-7:05 am

1 stop34h 05m

$1,129

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 7/23

8:55 am-11:43 pm

2 stops29h 48m

Chicago O'Hare Intl

Tue 8/19

1:30 am-6:20 am

1 stop37h 50m

$1,217

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 7/17

9:10 am-3:44 pm

1 stop21h 34m

Chicago O'Hare Intl

Mon 7/28

10:17 pm-7:05 am

1 stop41h 48m

$1,232

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/8

10:20 am-10:07 pm

2 stops27h 47m

Chicago O'Hare Intl

Thu 10/16

8:55 am-8:20 am

2 stops31h 25m

$1,275

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 7/19

2:05 pm-2:25 pm

1 stop39h 20m

Chicago O'Hare Intl

Wed 7/30

4:00 pm-10:50 am

1 stop27h 50m

$1,360

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 7/19

9:40 pm-5:40 am

2 stops47h 00m

Chicago O'Hare Intl

Wed 7/30

6:00 am-7:45 pm

2 stops46h 45m

$1,462

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 23 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 June 9, 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 June 12, 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 June 12, 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
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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
64 reviews
Air Tahiti Nui
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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
1,088 reviews
Air Tahiti Nui
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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
1,489 reviews
Air Tahiti Nui
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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
882 reviews
Air Tahiti Nui
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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
7,950 reviews
Air Tahiti Nui
8.7
Very good
64 reviews

Boarding

8.7

Food

7.8

Crew

9.0

Comfort

8.1

Overall

8.7

Entertainment

7.3

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, Delta ($1,093), ANA ($1,115), and American Airlines ($1,129) 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 American Airlines ($760), Air Canada ($793), and Delta ($864).

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$762FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,296FlexibilityNo cancel feeOn-time71%

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