Find flights
When to book
Airlines
FAQs

Cheap flights from Sydney to Chicago from $685

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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
6 Sep — 13 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Sydney to Chicago

Enter your travel dates to find the best prices.

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 7 August 2026.

Tue 8/906:15 -
2 stops39h 02m
Tue 22/906:20 -
3 stops49h 05m
Deal found 1/8$1,197
Tue 8/909:20 -
1 stop20h 23m
Tue 22/915:40 -
1 stop24h 40m
Deal found 2/8$1,324
Mon 30/1111:20 -
2 stops46h 30m
Mon 8/210:40 -
2 stops29h 55m
Deal found 3/8$1,329
Mon 9/1111:20 -
2 stops37h 40m
Mon 30/1113:55 -
2 stops26h 40m
Deal found 2/8$1,334
Tue 8/909:15 -
2 stops24h 04m
Tue 22/914:00 -
2 stops25h 50m
Deal found 3/8$2,172
Sat 29/809:15 -
2 stops23h 46m
Sat 5/910:56 -
2 stops28h 54m
Deal found 1/8$2,319
Fri 18/912:00 -
1 stop38h 59m
Fri 25/912:54 -
1 stop27h 01m
Deal found 4/8$2,360
Tue 10/1110:40 -
2 stops24h 24m
Wed 25/1113:22 -
2 stops26h 08m
Deal found 6/8$2,450
Tue 10/1110:40 -
2 stops22h 59m
Thu 26/1112:30 -
2 stops27h 00m
Deal found 6/8$2,487
Tue 10/1110:40 -
2 stops22h 59m
Thu 12/1113:22 -
2 stops26h 08m
Deal found 6/8$2,524
Thu 24/909:15 -
2 stops28h 29m
Thu 15/1013:27 -
2 stops26h 23m
Deal found 2/8$2,532
Sun 1/1110:40 -
2 stops24h 20m
Wed 18/1113:22 -
2 stops26h 08m
Deal found 6/8$2,676

Find 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 7 August 2026.

Round-trip from

$1,197

One-way from

$685

Popular in

July

Cheapest in

August

Average price

$1,534
8/9-22/9
  • 8/9-22/9
  • 5 total stops
  • 88h 07m total
  • Sydney to Chicago
Search Deals
8/10
  • 8/10
  • 3 total stops
  • 37h 42m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($70 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($35 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Customise 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 647,157 searches. Data last updated 7 August 2026.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:20-16:35

2 stops22h 15m

Chicago O'Hare Intl

Tue 22/9

15:40-07:20

1 stop24h 40m

$1,332

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 17/9

09:20-14:52

2 stops44h 32m

Chicago O'Hare Intl

Thu 24/9

15:40-07:20

1 stop24h 40m

$1,496

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 29/8

09:55-21:32

2 stops26h 37m

Chicago O'Hare Intl

Sat 5/9

16:11-10:40

2 stops27h 29m

$2,004

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 10/11

11:05-12:55

1 stop42h 50m

Chicago O'Hare Intl

Wed 25/11

14:35-19:15

2 stops35h 40m

$2,008

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

18:55-14:20

2 stops34h 25m

Chicago O'Hare Intl

Fri 18/9

16:15-06:10

1 stop46h 55m

$2,120

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 14/9

09:10-19:59

1 stop25h 49m

Chicago O'Hare Intl

Tue 29/9

15:20-07:05

1 stop24h 45m

$2,145
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 23/8

09:10-14:54

1 stop20h 44m

Chicago O'Hare Intl

Mon 7/9

19:00-07:05

1 stop21h 05m

$2,174

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 27/9

10:20-14:50

1 stop19h 30m

Chicago O'Hare Intl

Sat 3/10

21:40-07:55

1 stop42h 15m

$2,245

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 10/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Tue 24/11

13:22-08:30

2 stops26h 08m

$2,450

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 2/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Tue 17/11

11:28-08:30

2 stops28h 02m

$2,450

Flights are sorted by cheapest return flights first.

Deals found on 1/8

Showing 1-10 of 36 resultsSorted by cheapest first
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 return 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

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 $1,494). Flying from Sydney to Chicago in July is currently the most expensive (average of $1,990). 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.

How much does it cost for a return flight from Sydney to Chicago?

Airfare is below average for this route at the moment.
Sydney to Chicago flights typically cost between $1,346 and $1,890 in September.
The cheapest return price found within the last 5 days was $1,197 on Multiple Airlines (8 Sept–22 Sept).

What’s the top stopover airport for flights from Sydney to Chicago?

Share of one-stop return flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Los Angeles (LAX) – chosen by Cheapflights users on 58% of one-stop itineraries from Sydney to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Sydney to Chicago?

Average return fare for one-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Dallas (DFW) is the most affordable one-stop option, with an average return flight price of $1,555.

What’s the fastest stopover option from Sydney to Chicago?

Shortest average travel time for one-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via San Francisco (SFO) have the shortest average one-way travel time for one-stop routes: 19h 35m.

Which airport typically offers the quickest stopover for flights from Sydney to Chicago?

Average stopover duration for one-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average stopover time of 1h 27m.

How far ahead should I book a flight from Sydney to Chicago?

Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 7 August 2026.
See what other customers who have flown with Air New Zealand,Qantas Airways, andUnited Airlines from Sydney to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Air New Zealand
8.0
Very Good
659 reviews
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Qantas Airways
7.5
Good
1,079 reviews
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
United Airlines
7.4
Good
10,075 reviews
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
American Airlines
7.1
Good
11,873 reviews
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Air Canada
7.1
Good
11,432 reviews
Air New Zealand
8.0
Very Good
659 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.4

Entertainment

7.4

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

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?

    For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.

  • How long is the flight from Sydney to Chicago?

    Airlines like Air Canada and Delta fly from Sydney to Chicago in about 22h 15m. The time it takes to get you to your destination can typically vary by up to 2h 09m. The distance between Sydney and Chicago is about 14851 km. Both multi-stop and direct flights can be found to your destination and back.

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

    Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,076. Other airlines that can offer you cheap pricing are Qantas Airways, from $1,253, and American Airlines, from $1,254. You may be able to fly from Sydney to Chicago for 37% 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 holiday 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 $1,494). Flying from Sydney to Chicago in July is currently the most expensive (average of $1,990). 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

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.

Fly from Sydney to Chicago on these airlines

Choose from the following airlines for your flight from Sydney to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 7 August 2026.
Qantas Airways flights from Sydney Kingsford Smith to Chicago
Air Canada flights from Sydney Kingsford Smith to Chicago
ANA flights from Sydney Kingsford Smith to Chicago

Top 5 airlines flying from Sydney to Chicago

Discover the top 5 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 647,157 searches. Data last updated 7 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$1,076Average$1,642FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Qantas AirwaysCheapest$1,253Average$1,719FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights
American AirlinesCheapest$1,254Average$1,624FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air New ZealandCheapest$1,344Average$1,526FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
United AirlinesCheapest$1,404Average$1,797FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Sydney to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Sydney to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Sydney to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Sydney.

Can Cheapflights find flights from Sydney to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Sydney to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?

Of course! You can now track prices for flights from Sydney to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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.