HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$425+ 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
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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.

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

Round-trip from

$868
(Gotogate)

One-way from

$425
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$1,148
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. 22% potential increase in price ($296 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 septiembre 15, 2025.

This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/811:20 amSYD - ORD
2 stops44h 50mAir Canada
sáb. 11/223:40 pmORD - SYD
1 stop24h 55mAir Canada
Deal found 9/15$868
This BestPriceTravel deal was found by Cheapflights users on 9/13. 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/309:20 amSYD - ORD
1 stop22h 22mAir Canada
mié. 11/123:40 pmORD - SYD
1 stop24h 55mAir Canada
Deal found 9/13$874
This Air Canada deal was found by Cheapflights users on 9/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/2910:20 amSYD - ORD
2 stops37h 40mAir Canada
mié. 11/53:40 pmORD - SYD
1 stop24h 55mAir Canada
Deal found 9/14$881
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:20 amSYD - ORD
1 stop20h 21mAir Canada
jue. 11/63:40 pmORD - SYD
1 stop24h 55mAir Canada
Deal found 9/15$883
This BestPriceTravel deal was found by Cheapflights users on 9/14. 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/510:20 amSYD - ORD
1 stop22h 22mAir Canada
mié. 12/243:40 pmORD - SYD
1 stop24h 55mAir Canada
Deal found 9/14$919
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3011:20 amSYD - MDW
2 stops41h 17mMultiple Airlines
jue. 11/66:25 amMDW - SYD
2 stops32h 00mMultiple Airlines
Deal found 9/15$966
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/309:25 amSYD - MDW
2 stops24h 10mDelta
mié. 11/121:14 pmMDW - SYD
2 stops26h 16mDelta
Deal found 9/15$1,004
This Delta deal was found by Cheapflights users on 9/14. 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.
mié. 10/299:40 amSYD - MDW
2 stops28h 34mDelta
mié. 11/51:08 pmMDW - SYD
2 stops26h 22mDelta
Deal found 9/14$1,213
This Delta deal was found by Cheapflights users on 9/14. 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.
jue. 10/309:40 amSYD - MDW
2 stops22h 29mDelta
jue. 11/610:40 amMDW - SYD
2 stops28h 50mDelta
Deal found 9/14$1,341
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/810:40 amSYD - MDW
2 stops24h 45mDelta
sáb. 11/229:32 amMDW - SYD
2 stops29h 58mDelta
Deal found 9/15$1,478
This Delta deal was found by Cheapflights users on 9/14. 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.
mié. 10/810:25 amSYD - MDW
2 stops23h 18mDelta
mar. 10/149:35 amMDW - SYD
2 stops30h 00mDelta
Deal found 9/14$1,489
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/189:25 amSYD - MDW
2 stops27h 11mDelta
vie. 10/179:35 amMDW - SYD
2 stops30h 00mDelta
Deal found 9/15$1,579

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 septiembre 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

sáb. 11/8

11:20 am-3:10 pm

2 stops44h 50m

Chicago O'Hare Intl

sáb. 11/22

3:40 pm-9:35 am

1 stop24h 55m

$868

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mar. 9/30

9:20 am-4:42 pm

1 stop22h 22m

Chicago O'Hare Intl

mié. 11/12

3:40 pm-9:35 am

1 stop24h 55m

$874

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 10/29

10:20 am-8:00 am

2 stops37h 40m

Chicago O'Hare Intl

mié. 11/5

3:40 pm-9:35 am

1 stop24h 55m

$881

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 3/4

11:20 am-8:05 am

3 stops37h 45m

Chicago O'Hare Intl

sáb. 3/7

12:50 pm-9:35 am

2 stops27h 45m

$922

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

vie. 10/31

10:20 am-5:10 pm

2 stops22h 50m

Chicago O'Hare Intl

dom. 11/2

8:45 am-9:35 am

2 stops31h 50m

$949

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

sáb. 10/11

10:20 am-3:00 pm

1 stop20h 40m

Chicago O'Hare Intl

sáb. 10/18

3:45 pm-8:20 am

1 stop24h 35m

$967

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 12/3

11:20 am-2:41 pm

1 stop20h 21m

Chicago O'Hare Intl

lun. 12/8

8:15 pm-6:55 am

2 stops41h 40m

$983

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 10/28

9:40 am-6:25 pm

2 stops24h 45m

Chicago Midway

mar. 11/4

10:40 am-8:30 am

2 stops28h 50m

$1,004

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 9/30

9:25 am-9:36 pm

2 stops27h 11m

Chicago Midway

mié. 11/12

12:47 pm-8:30 am

2 stops26h 43m

$1,004

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 12/3

10:40 am-8:04 am

2 stops38h 24m

Chicago O'Hare Intl

lun. 12/8

10:46 am-8:30 am

2 stops28h 44m

$1,004

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 33 results
1
2
3
4

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 September 12, 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 septiembre 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.

How much does it cost to fly round-trip from Sydney to Chicago?

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 septiembre 15, 2025.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
905 reviews

Comfort

7.5

Overall

7.5

Food

6.9

Boarding

7.7

Crew

8.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

SYD - BNE

Great. Except I haven’t claimed my free lounge passes since 2022 on my Qantas credit card. That’s lots of flights I would have booked if you’d reminded me
Qantas Airways
7.5
Good
905 reviews
Qantas Airways
7.5
Good
905 reviews

Comfort

7.5

Overall

7.5

Food

6.9

Boarding

7.7

Crew

8.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

SYD - BNE

Great. Except I haven’t claimed my free lounge passes since 2022 on my Qantas credit card. That’s lots of flights I would have booked if you’d reminded me
American Airlines
7.2
Good
10,000 reviews
Qantas Airways
7.5
Good
905 reviews

Comfort

7.5

Overall

7.5

Food

6.9

Boarding

7.7

Crew

8.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

SYD - BNE

Great. Except I haven’t claimed my free lounge passes since 2022 on my Qantas credit card. That’s lots of flights I would have booked if you’d reminded me

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.

  • How long is the flight from Sydney to Chicago?

    For as low as $1,004, Air Canada can have you in Chicago from Sydney in 24h 45m. The distance from Sydney to Chicago is about 9234 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Qantas Airways ($631), and American Airlines ($884) offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 38% less than the average price by searching for these airlines.

  • 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
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 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$631Average$762FlexibilityNo cancel feeOn-time74%
American AirlinesCheapest$884Average$1,129FlexibilityNo cancel feeOn-time71%

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.