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Cheap flights from Sydney to Chicago from $948

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
23 Jul — 30 Jul1
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 23 June 2026.

Wed 12/806:05
SYD
-
ORD
2 stops39h 12m
Multiple Airlines
Wed 19/809:20
ORD
-
SYD
3 stops35h 30m
Multiple Airlines
Deal found 22/6$1,309
Mon 3/813:15
SYD
-
MDW
3 stops36h 52m
Multiple Airlines
Mon 17/811:06
MDW
-
SYD
3 stops33h 44m
Multiple Airlines
Deal found 20/6$1,356
Mon 27/713:15
SYD
-
ORD
2 stops32h 02m
Multiple Airlines
Mon 10/810:16
ORD
-
SYD
3 stops34h 34m
Multiple Airlines
Deal found 19/6$1,393
Mon 3/813:15
SYD
-
ORD
2 stops32h 02m
Multiple Airlines
Mon 17/807:15
ORD
-
SYD
3 stops37h 35m
Multiple Airlines
Deal found 20/6$1,409
Mon 3/813:15
SYD
-
ORD
2 stops32h 02m
Multiple Airlines
Mon 10/810:16
ORD
-
SYD
3 stops44h 54m
Multiple Airlines
Deal found 19/6$1,445
Thu 3/913:15
SYD
-
ORD
2 stops32h 02m
Multiple Airlines
Sun 20/913:02
ORD
-
SYD
3 stops31h 48m
Multiple Airlines
Deal found 22/6$1,469
Sat 5/917:50
SYD
-
ORD
1 stop36h 04m
Qantas Airways
Sun 6/917:05
ORD
-
SYD
1 stop22h 20m
Qantas Airways
Deal found 22/6$1,493
Tue 11/809:10
SYD
-
ORD
1 stop36h 07m
Multiple Airlines
Tue 15/906:50
ORD
-
SYD
2 stops33h 15m
Multiple Airlines
Deal found 18/6$1,548
Wed 11/1109:55
SYD
-
ORD
2 stops28h 39m
Air New Zealand
Mon 16/1113:00
ORD
-
SYD
2 stops28h 30m
Air New Zealand
Deal found 22/6$1,559
Mon 17/811:55
SYD
-
ORD
2 stops26h 31m
Air New Zealand
Mon 24/816:20
ORD
-
SYD
2 stops27h 20m
Air New Zealand
Deal found 18/6$1,563
Sun 2/814:10
SYD
-
ORD
2 stops31h 07m
Multiple Airlines
Sun 9/809:20
ORD
-
SYD
3 stops35h 30m
Multiple Airlines
Deal found 18/6$1,585
Thu 3/909:15
SYD
-
MDW
2 stops24h 18m
Delta
Sun 20/909:29
MDW
-
SYD
2 stops30h 21m
Delta
Deal found 22/6$1,675

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 23 June 2026.

Round-trip from

$1,356

One-way from

$948

Popular in

May

Cheapest in

August

Average price

$1,886
3/8-17/8
  • 3/8-17/8
  • 6 total stops
  • 70h 36m total
  • Sydney to Chicago
Search Deals
12/8
  • 12/8
  • 3 total stops
  • 50h 02m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($234 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($34 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 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 23 June 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 - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/11

11:45-23:02

2 stops28h 17m

Chicago O'Hare Intl

Mon 16/11

14:10-08:45

2 stops25h 35m

$1,640

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/9

09:15-18:33

2 stops24h 18m

Chicago Midway

Sun 20/9

09:29-06:50

2 stops30h 21m

$1,675

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 3/9

09:15-18:19

2 stops24h 04m

Chicago O'Hare Intl

Sun 20/9

13:55-06:50

2 stops25h 55m

$1,675
Fastest return journey

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 29/9

09:15-18:45

2 stops24h 30m

Chicago O'Hare Intl

Tue 13/10

18:30-07:50

1 stop21h 20m

$1,679

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 12/9

09:15-21:19

1 stop27h 04m

Chicago O'Hare Intl

Sat 3/10

09:30-06:50

1 stop30h 20m

$1,819

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 21/11

10:40-17:21

1 stop23h 41m

Chicago O'Hare Intl

Thu 3/12

08:55-08:30

2 stops30h 35m

$1,819

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/11

11:35-05:40

2 stops35h 05m

Chicago O'Hare Intl

Mon 16/11

22:45-09:45

1 stop42h 00m

$1,969

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/11

11:15-06:43

1 stop36h 28m

Chicago O'Hare Intl

Sun 15/11

13:32-06:25

1 stop23h 53m

$1,975

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 21/11

21:40-07:00

3 stops26h 20m

Chicago O'Hare Intl

Thu 3/12

17:55-19:45

2 stops32h 50m

$2,023

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 11/8

20:45-12:03

3 stops30h 18m

Chicago O'Hare Intl

Tue 15/9

19:00-18:50

2 stops32h 50m

$2,053

Flights are sorted by cheapest return flights first.

Deals found on 22/6

Showing 1-10 of 31 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

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 $668). Flying from Sydney to Chicago in July is currently the most expensive (average of $1,314). 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 55% 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 $1,563.

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 30m.

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 23 June 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
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding
Air New Zealand
8.0
Very Good
645 reviews
Air New Zealand
8.0
Very Good
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding
Qantas Airways
7.5
Good
1,050 reviews
Air New Zealand
8.0
Very Good
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding
United Airlines
7.4
Good
9,874 reviews
Air New Zealand
8.0
Very Good
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding
American Airlines
7.1
Good
11,744 reviews
Air New Zealand
8.0
Very Good
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding
Air Canada
7.1
Good
11,244 reviews
Air New Zealand
8.0
Very Good
645 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.4

Crew

8.5

Entertainment

7.4

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

SIN - AKL

We were stuck on tarmac for an hour after boarding

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 New Zealand and Delta fly from Sydney to Chicago in about 24h 18m. The time it takes to get you to your destination can typically vary by up to 3h 59m. 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 $1,081. Other airlines that can offer you cheap pricing are Qantas Airways, from $1,260, and American Airlines, from $1,261. 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, December is the cheapest month in which you can book a flight from Sydney to Chicago (average of $668). Flying from Sydney to Chicago in July is currently the most expensive (average of $1,314). 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 23 June 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 23 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$1,081Average$1,692FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Qantas AirwaysCheapest$1,260Average$1,703FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights
American AirlinesCheapest$1,261Average$1,633FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air New ZealandCheapest$1,351Average$1,510FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
United AirlinesCheapest$1,412Average$1,938FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
ANACheapest$1,526Average$1,956FlexibilityNo 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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