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Cheap flights from Sydney to Chicago from $686

SYD — CHI
9 Dec — 16 Dec1
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

Thu 12/1114:00 -
3 stops27h 21m
Wed 25/1107:49 -
3 stops35h 46m
Deal found 6/11$1,671
Thu 12/1122:20 -
1 stop31h 10m
Wed 25/1114:10 -
1 stop26h 25m
Deal found 6/11$1,795
Thu 19/1108:45 -
1 stop44h 45m
Wed 2/1214:10 -
1 stop26h 25m
Deal found 6/11$1,802
Thu 19/1111:55 -
2 stops27h 34m
Wed 2/1214:29 -
2 stops27h 06m
Deal found 6/11$1,889
Sun 22/1111:30 -
1 stop46h 25m
Fri 11/1222:45 -
1 stop42h 05m
Deal found 4/11$2,006
Mon 16/1111:05 -
1 stop42h 25m
Thu 3/1214:10 -
1 stop29h 50m
Deal found 7/11$2,079
Tue 24/1111:30 -
1 stop46h 25m
Wed 9/1222:45 -
1 stop42h 05m
Deal found 4/11$2,083
Thu 19/1122:20 -
1 stop31h 10m
Wed 2/1207:00 -
2 stops30h 25m
Deal found 6/11$2,089

Find flight deals from Sydney to Chicago

Round-trip from

$1,802

One-way from

$686

Popular in

May

Cheapest in

October

Average price

$1,769
Cathay Pacific
  • Cathay Pacific
  • 19/11-2/12
  • 2 total stops
  • 71h 10m total
  • Sydney to Chicago
Search Deals
28/2-31/12
  • 28/2-31/12
  • 2 total stops
  • 42h 05m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($231 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($74 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2026
Search Deals

Cheapflights Fare Finder

 
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

Fri 5/3

14:00-18:55

3 stops45h 55m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$882

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 20/3

14:00-06:10

3 stops32h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$981

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 7/12

11:00-00:54

3 stops54h 54m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,216
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 4/12

21:40-05:37

3 stops24h 57m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,438

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 10/12

21:40-05:37

3 stops24h 57m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,671

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 26/11

11:15-06:14

1 stop35h 59m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,734

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 17/12

07:35-14:30

3 stops47h 55m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,831

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 17/12

08:45-12:30

1 stop44h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,865

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 19/12

21:40-23:59

2 stops43h 19m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,897

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 18/12

17:30-14:30

2 stops38h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,945

Flights are sorted by cheapest return flights first.

Deals found on 4/11

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
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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

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, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,547). Flying from Sydney to Chicago in December is currently the most expensive (average of $2,313). 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 typical for this route at the moment.
Sydney to Chicago flights typically cost between $1,157 and $2,041 in November.
The cheapest return price found within the last 5 days was $1,802 on Cathay Pacific (19 Nov–2 Dec).

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

Los Angeles (LAX) – chosen by Cheapflights users on 60% of one-stop itineraries from Sydney to Chicago on Cheapflights.

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

Nadi (NAN) is the most affordable one-stop option, with an average return flight price of $807.

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

Flights via Nadi (NAN) have the shortest average one-way travel time for one-stop routes: 16h 57m.

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

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 81 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

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
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.
Air New Zealand
8.0
Very Good
683 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.
Qantas Airways
7.5
Good
1,123 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.
United Airlines
7.3
Good
10,476 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.
Air Canada
7.1
Good
11,876 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.
American Airlines
7.0
Good
12,226 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.5

Food

7.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Blair,Oct 2026

WLG - AKL

The chicken dish was okay but kind of weird unlike the chicken penne on my trip home which was delicious.

Related info for your journey

  • 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 Cathay Pacific, Turkish Airlines, and Qantas Airways fly from Sydney to Chicago in about 23h 35m. The time it takes to get you to your destination can typically vary by up to 23h 50m. 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 $974. Other airlines that can offer you cheap pricing are American Airlines, from $976, and Delta, from $1,076. You may be able to fly from Sydney to Chicago for 48% 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, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,547). Flying from Sydney to Chicago in December is currently the most expensive (average of $2,313). 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

Fly from Sydney to Chicago on these airlines

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

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$974Average$1,610FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapest$976Average$1,101FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$1,076Average$1,868FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air New ZealandCheapest$1,376Average$1,891FlexibilityNo cancel feeOn-time78%
Search Air New Zealand flights
United AirlinesCheapest$1,439Average$1,925FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Qantas AirwaysCheapest$1,559Average$1,957FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights

Fly with Cheapflights

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.

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