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Cheap flights from Sydney to Chicago from $779

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
10 Jun — 17 Jun1
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 11 May 2026.

Tue 8/909:10
SYD
-
ORD
2 stops25h 42m
American Airlines
Mon 21/919:01
ORD
-
SYD
1 stop21h 04m
American Airlines
Deal found 11/5$1,425
Thu 10/909:15
SYD
-
ORD
2 stops24h 24m
Delta
Mon 21/915:50
ORD
-
SYD
2 stops24h 00m
Delta
Deal found 11/5$1,451
Thu 10/909:10
SYD
-
ORD
1 stop22h 35m
American Airlines
Thu 24/919:01
ORD
-
SYD
1 stop21h 04m
American Airlines
Deal found 9/5$1,493
Thu 3/909:10
SYD
-
ORD
2 stops24h 25m
American Airlines
Sat 12/917:09
ORD
-
SYD
2 stops22h 56m
American Airlines
Deal found 7/5$1,494
Fri 11/909:10
SYD
-
ORD
1 stop21h 40m
American Airlines
Sun 20/919:01
ORD
-
SYD
1 stop21h 04m
American Airlines
Deal found 11/5$1,495
Thu 1/1009:10
SYD
-
ORD
1 stop30h 19m
American Airlines
Fri 9/1020:25
ORD
-
SYD
1 stop43h 05m
American Airlines
Deal found 9/5$1,502
Thu 10/909:10
SYD
-
ORD
1 stop22h 35m
Qantas Airways
Thu 24/915:52
ORD
-
SYD
1 stop24h 13m
Qantas Airways
Deal found 9/5$1,505
Sat 12/912:00
SYD
-
ORD
1 stop21h 24m
American Airlines
Mon 21/919:01
ORD
-
SYD
1 stop21h 04m
American Airlines
Deal found 11/5$1,506
Sun 22/1111:15
SYD
-
ORD
1 stop29h 44m
Qantas Airways
Sun 29/1111:45
ORD
-
SYD
1 stop25h 40m
Qantas Airways
Deal found 10/5$1,515
Sat 12/912:00
SYD
-
ORD
1 stop21h 24m
American Airlines
Sat 19/920:55
ORD
-
SYD
1 stop43h 00m
American Airlines
Deal found 11/5$1,516
Mon 7/912:00
SYD
-
ORD
1 stop21h 35m
American Airlines
Sat 19/918:02
ORD
-
SYD
1 stop21h 53m
American Airlines
Deal found 10/5$1,517
Thu 10/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Thu 24/913:05
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 9/5$1,519

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 11 May 2026.

Round-trip from

$1,425

One-way from

$779

Popular in

December

Cheapest in

August

Average price

$1,608
American Airlines
  • American Airlines
  • 8/9-20/9
  • 2 total stops
  • 43h 38m total
  • Sydney to Chicago
Search Deals
25/8
  • 25/8
  • 2 total stops
  • 32h 04m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($66 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($27 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 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 11 May 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 - MDW

SYDMDW

Sydney Kingsford Smith

Mon 19/10

10:15-18:37

2 stops24h 22m

Chicago Midway

Sat 31/10

13:00-07:30

2 stops26h 30m

$1,520

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 25/8

09:15-18:33

2 stops24h 18m

Chicago Midway

Thu 1/10

13:00-06:50

2 stops26h 50m

$2,015

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 8/6

06:25-16:41

2 stops25h 16m

Chicago O'Hare Intl

Mon 15/6

15:50-06:55

1 stop24h 05m

$2,091

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 4/6

20:45-18:50

2 stops37h 05m

Chicago O'Hare Intl

Wed 12/8

20:20-18:50

2 stops31h 30m

$2,195

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 30/5

20:45-13:14

2 stops31h 29m

Chicago O'Hare Intl

Fri 12/6

17:42-18:50

2 stops34h 08m

$2,293

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/6

20:45-06:20

3 stops24h 35m

Chicago O'Hare Intl

Wed 10/6

20:05-18:50

2 stops31h 45m

$2,308

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 22/5

20:45-18:50

2 stops37h 05m

Chicago O'Hare Intl

Sun 31/5

19:49-18:50

2 stops32h 01m

$2,335

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/6

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 10/6

13:49-06:50

2 stops26h 01m

$2,348

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 11/6

20:45-05:00

2 stops23h 15m

Chicago O'Hare Intl

Thu 23/7

17:42-18:50

2 stops34h 08m

$2,364

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/6

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 12/8

10:54-06:50

2 stops28h 56m

$2,367

Flights are sorted by cheapest return flights first.

Deals found on 6/5

Showing 1-10 of 38 resultsSorted by cheapest first
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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 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?

Booking 36 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, December is the cheapest month in which you can book a flight from Sydney to Chicago (average of $646). Flying from Sydney to Chicago in February is currently the most expensive (average of $1,193). 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?

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 54% 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 $1,510.

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 11 May 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
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
ANA
8.3
Very Good
1,208 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Air New Zealand
8.0
Very Good
642 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Qantas Airways
7.5
Good
1,035 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
United Airlines
7.4
Good
9,701 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Air Canada
7.1
Good
11,019 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Boarding

8.5

Food

7.7

Overall

8.3

Entertainment

8.0

Comfort

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.

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 Delta and Qantas Airways fly from Sydney to Chicago in about 24h 22m. The time it takes to get you to your destination can typically vary by up to 54m. 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 $1,045. Other airlines that can offer you cheap pricing are American Airlines, from $1,076, and Qantas Airways, from $1,217. You may be able to fly from Sydney to Chicago for 35% 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, December is the cheapest month in which you can book a flight from Sydney to Chicago (average of $646). Flying from Sydney to Chicago in February is currently the most expensive (average of $1,193). 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 11 May 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 11 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$1,045Average$1,707FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapest$1,076Average$1,122FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Qantas AirwaysCheapest$1,217Average$1,633FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights
Air New ZealandCheapest$1,305Average$1,459FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
United AirlinesCheapest$1,364Average$1,872FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
ANACheapest$1,449Average$1,706FlexibilityNo 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.

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