Find flights
When to book
Airlines
FAQs

Cheap flights from Sydney to Chicago from $557

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
11 Mar — 18 Mar1
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 9 February 2026.

Mon 2/311:20
SYD
-
ORD
1 stop20h 21m
Air Canada
Mon 16/315:35
ORD
-
SYD
1 stop25h 00m
Air Canada
Deal found 8/2$1,097
Mon 5/1010:20
SYD
-
ORD
1 stop20h 28m
Air Canada
Thu 22/1008:45
ORD
-
SYD
2 stops31h 35m
Air Canada
Deal found 6/2$1,136
Thu 5/311:20
SYD
-
ORD
1 stop20h 21m
Air Canada
Wed 18/307:15
ORD
-
SYD
2 stops33h 20m
Air Canada
Deal found 6/2$1,137
Thu 19/310:25
SYD
-
ORD
2 stops37h 35m
Air Canada
Tue 21/408:42
ORD
-
SYD
2 stops31h 38m
Air Canada
Deal found 6/2$1,141
Tue 6/1010:20
SYD
-
ORD
2 stops25h 52m
Air Canada
Mon 12/1008:45
ORD
-
SYD
2 stops31h 35m
Air Canada
Deal found 7/2$1,146
Thu 12/310:25
SYD
-
ORD
1 stop20h 16m
Air Canada
Thu 19/307:15
ORD
-
SYD
2 stops33h 20m
Air Canada
Deal found 6/2$1,148
Wed 11/210:40
SYD
-
MDW
2 stops23h 49m
Delta
Wed 18/213:28
MDW
-
SYD
2 stops26h 02m
Delta
Deal found 6/2$1,550
Thu 5/310:40
SYD
-
MDW
2 stops25h 00m
Delta
Wed 18/314:05
MDW
-
SYD
2 stops25h 20m
Delta
Deal found 6/2$1,552
Mon 2/314:15
SYD
-
MDW
2 stops25h 16m
Delta
Mon 16/313:10
MDW
-
SYD
2 stops26h 15m
Delta
Deal found 7/2$1,554
Thu 12/313:15
SYD
-
MDW
2 stops25h 16m
Delta
Thu 19/314:05
MDW
-
SYD
2 stops25h 25m
Delta
Deal found 6/2$1,626
Fri 27/309:40
SYD
-
MDW
2 stops25h 00m
Delta
Sat 4/413:10
MDW
-
SYD
2 stops26h 40m
Delta
Deal found 7/2$1,704
Wed 7/1010:15
SYD
-
MDW
2 stops24h 22m
Delta
Tue 13/1013:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 6/2$1,720

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 9 February 2026.

Round-trip from

$1,097

One-way from

$557

Popular in

December

Cheapest in

April

Average price

$1,537
Air Canada
  • Air Canada
  • 2/3-16/3
  • 2 total stops
  • 45h 21m total
  • Sydney to Chicago
Search Deals
28/4
  • 28/4
  • 2 total stops
  • 31h 35m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($349 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($56 potential savings vs. average return price).
Search Deals
Average for round-trip flights in February 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 9 February 2026.
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 19/3

10:25-08:00

2 stops37h 35m

Chicago O'Hare Intl

Tue 21/4

08:42-07:20

2 stops31h 38m

$1,141

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 12/3

10:25-14:41

1 stop20h 16m

Chicago O'Hare Intl

Thu 19/3

07:15-08:35

2 stops33h 20m

$1,148

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/3

11:20-20:00

1 stop25h 40m

Chicago O'Hare Intl

Wed 18/3

15:35-08:35

1 stop25h 00m

$1,165

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 17/6

09:20-20:05

2 stops25h 45m

Chicago O'Hare Intl

Wed 24/6

09:50-07:20

2 stops30h 30m

$1,173

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 26/2

11:20-09:13

2 stops38h 53m

Chicago O'Hare Intl

Fri 13/3

15:35-08:40

2 stops49h 05m

$1,271

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 22/6

09:20-07:50

2 stops37h 30m

Chicago O'Hare Intl

Sun 19/7

15:40-07:20

1 stop24h 40m

$1,284

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-18:40

2 stops25h 00m

Chicago Midway

Tue 21/4

12:53-06:50

2 stops26h 57m

$1,552

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/3

10:40-18:40

2 stops25h 00m

Chicago Midway

Wed 18/3

14:05-07:25

2 stops25h 20m

$1,552

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 24/3

13:15-22:31

2 stops25h 16m

Chicago Midway

Tue 31/3

14:05-07:50

2 stops25h 45m

$1,552

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/3

14:15-22:31

2 stops25h 16m

Chicago Midway

Mon 16/3

13:10-07:25

2 stops26h 15m

$1,554

Flights are sorted by cheapest return flights first.

Deals found on 6/2

Showing 1-10 of 25 results
1
2
3

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

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

Use this chart to determine the optimal time to book a return flight from Sydney to Chicago. Price data was last updated on 6 February 2026.

Booking 87 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.

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 $883). Flying from Sydney to Chicago in January is currently the most expensive (average of $1,874). 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’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 65% 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 $1,560.

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 San Francisco (SFO) offer the fastest connection on this route, with an average stopover time of 1h 35m.

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 9 February 2026.
See what other customers who have flown with ANA, Air New Zealand, andQantas Airways 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.
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
ANA
8.4
Very Good
1,089 reviews
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
Air New Zealand
8.0
Very Good
582 reviews
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
Qantas Airways
7.5
Good
988 reviews
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
United Airlines
7.4
Good
9,259 reviews
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!
Air Canada
7.1
Good
10,698 reviews
ANA
8.4
Very Good
1,089 reviews
Check prices

Entertainment

7.9

Overall

8.4

Boarding

8.6

Comfort

8.2

Crew

8.7

Food

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

BKK - NRT

Really enjoyed fly with ANA for our first time. Thank you!

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. 6 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 25h. The time it takes to get you to your destination can typically vary by up to 12h 35m. The distance between Sydney and Chicago is about 14861 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 $936. Other airlines that can offer you cheap pricing are Air Canada, from $1,080, and American Airlines, from $1,111. 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 $883). Flying from Sydney to Chicago in January is currently the most expensive (average of $1,874). 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 9 February 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 6 airlines flying from Sydney to Chicago

Discover the top 6 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 9 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$936Average$1,083FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights
Air CanadaCheapest$1,080Average$1,547FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapest$1,111Average$1,158FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air New ZealandCheapest$1,348Average$1,507FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
United AirlinesCheapest$1,409Average$2,131FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
ANACheapest$1,497Average$1,615FlexibilityNo cancel feeOn-time80%
Search ANA 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.