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Cheap flights from Sydney to Chicago from $686

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 8/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Sydney to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
13:15 - 06:17SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
32h 02m2 stops Nadi Los Angeles
Multiple Airlines Logo
06:30 - 22:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
48h 55m3 stops Denver Intl Los Angeles Nadi
$1,188Multiple Airlines
Tue, 8 Sep - Tue, 22 Sep
Multiple Airlines Logo
06:15 - 06:17SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
39h 02m2 stops Nadi Los Angeles
Multiple Airlines Logo
06:20 - 22:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
49h 05m3 stops Atlanta Hartsfield-Jackson Los Angeles Nadi
$1,199Multiple Airlines
Tue, 8 Sep - Tue, 22 Sep
Air Canada Logo
09:20 - 14:43SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 23m1 stop Vancouver Intl
Air Canada Logo
15:40 - 07:20ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 40m1 stop Vancouver Intl
$1,311Air Canada
Tue, 8 Sep - Tue, 22 Sep
Air Canada Logo
09:20 - 14:43SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 23m1 stop Vancouver Intl
Air Canada Logo
15:40 - 07:20ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 40m1 stop Vancouver Intl
$1,326Air Canada
Tue, 8 Sep - Tue, 22 Sep
Qantas Airways Logo
22:00 - 23:00SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
40h 00m2 stops Melbourne Los Angeles
Qantas Airways Logo
15:54 - 08:15ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 21m2 stops Dallas/Fort Worth Melbourne
$1,886Qantas Airways
Fri, 21 Aug - Sat, 5 Sep
Air New Zealand Logo
09:55 - 21:32SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 37m2 stops Auckland Intl Houston George Bush Intcntl
Air New Zealand Logo
16:11 - 10:40ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
27h 29m2 stops Houston George Bush Intcntl Auckland Intl
$2,007Air New Zealand
Sat, 29 Aug - Sat, 5 Sep
American Airlines Logo
09:10 - 18:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 55m1 stop Los Angeles
American Airlines Logo
19:03 - 08:05ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 02m1 stop Los Angeles
$2,148American Airlines
Thu, 24 Sep - Sun, 4 Oct
American Airlines Logo
09:10 - 19:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 49m1 stop Los Angeles
American Airlines Logo
15:20 - 07:05ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 45m1 stop Los Angeles
$2,148American Airlines
Mon, 14 Sep - Tue, 29 Sep
Qantas Airways Logo
09:10 - 14:54SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 44m1 stop Los Angeles
Qantas Airways Logo
19:00 - 07:05ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 05m1 stop Los Angeles
$2,178Qantas Airways
Sun, 23 Aug - Mon, 7 Sep
Air New Zealand Logo
19:25 - 19:14SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
40h 49m2 stops Auckland Intl Houston George Bush Intcntl
Air New Zealand Logo
16:05 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
23h 30m2 stops Houston George Bush Intcntl Auckland Intl
$2,535Air New Zealand
Sun, 10 Jan - Sun, 17 Jan

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Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
8 Sept
SYD09:20Sydney Kingsford Smith
20h 23m
1 stop
ORD14:43Chicago O'Hare Intl
22 Sept
ORD15:40Chicago O'Hare Intl
24h 40m
1 stop
SYD07:20Sydney Kingsford Smith
$1,326
Air Canada
8 Sept
SYD09:20Sydney Kingsford Smith
20h 23m
1 stop
ORD14:43Chicago O'Hare Intl
22 Sept
ORD15:40Chicago O'Hare Intl
24h 40m
1 stop
SYD07:20Sydney Kingsford Smith
$1,327
Air Canada
30 Nov
SYD11:20Sydney Kingsford Smith
46h 30m
2 stops
ORD16:50Chicago O'Hare Intl
8 Feb
ORD10:40Chicago O'Hare Intl
29h 55m
2 stops
SYD09:35Sydney Kingsford Smith
$1,331

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
11 Aug
SYD11:45Sydney Kingsford Smith
35h 55m
1 stop
ORD08:40Chicago O'Hare Intl
12 Aug
ORD17:45Chicago O'Hare Intl
24h 40m
1 stop
SYD09:25Sydney Kingsford Smith
$2,751
ANA
11 Aug
SYD11:45Sydney Kingsford Smith
35h 55m
1 stop
ORD08:40Chicago O'Hare Intl
12 Aug
ORD19:50Chicago O'Hare Intl
32h 20m
2 stops
SYD19:10Sydney Kingsford Smith
$2,755
ANA
8 Aug
SYD20:55Sydney Kingsford Smith
26h 45m
1 stop
ORD08:40Chicago O'Hare Intl
15 Aug
ORD17:45Chicago O'Hare Intl
34h 25m
1 stop
SYD19:10Sydney Kingsford Smith
$7,974

momondo 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, momondo users made 78,305 searches. Data last updated 5 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

13:15-06:17

2 stops32h 02m

Chicago O'Hare Intl

Tue 22/9

06:30-22:25

3 stops48h 55m

$1,188

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

06:15-06:17

2 stops39h 02m

Chicago O'Hare Intl

Tue 22/9

06:20-22:25

3 stops49h 05m

$1,199

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:20-14:43

1 stop20h 23m

Chicago O'Hare Intl

Tue 22/9

15:40-07:20

1 stop24h 40m

$1,311

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:20-14:43

1 stop20h 23m

Chicago O'Hare Intl

Tue 22/9

15:40-07:20

1 stop24h 40m

$1,326

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 21/8

22:00-23:00

2 stops40h 00m

Chicago O'Hare Intl

Sat 5/9

15:54-08:15

2 stops25h 21m

$1,886

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

$2,007

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 24/9

09:10-18:05

1 stop23h 55m

Chicago O'Hare Intl

Sun 4/10

19:03-08:05

1 stop21h 02m

$2,148

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

$2,148
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

$2,178

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 10/1

19:25-19:14

2 stops40h 49m

Chicago O'Hare Intl

Sun 17/1

16:05-08:35

2 stops23h 30m

$2,535

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Chicago from

How to get the cheapest flight ticket from Sydney to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Sydney and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $1,348 to $1,893.
The lowest price recently found on this route was $1,188.

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in September, then you should wait until October to fly from Sydney, when ticket prices are also cheap, with an average price of $1,519.

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

You are more likely to see cheaper flights to Chicago from Sydney when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,949 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sydney for as low as $1,461 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Sydney to Chicago flight.

How have Sydney to Chicago flight prices changed over time?

As of August 2026, prices for Sydney to Chicago flights are approximately 22% cheaper when compared to flights at the same time last year.

When to book flights from Sydney to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Sydney to Chicago (SYD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago

Fastest flight time

20h 10m

Direct flights

None
The fastest flight from Sydney to Chicago takes 20h 10m
There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.
Search flight deals

Frequently asked questions about flying from Sydney to Chicago

  • How far is Sydney Kingsford Smith to Chicago by plane?

    There are 14866.2 km between Sydney Kingsford Smith and Chicago. 20h 10m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago?

    Prices for flights from Sydney Kingsford Smith Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Sydney Kingsford Smith Airport to Chicago?

  • How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Sydney Kingsford Smith Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Sydney to Chicago?

Best airlines flying from Sydney to Chicago

Compare and see reviews for airlines that fly from Sydney to Chicago with momondo
Airline
Rating
Free cancellation
Price
Air CanadaPriceFrom $1,077Free cancellationRating
7.1
11,428 reviews
Search Air Canada flights
Qantas AirwaysPriceFrom $1,255Free cancellationRating
7.5
1,079 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,256Free cancellationRating
7.1
11,852 reviews
Search American Airlines flights
Air New ZealandPriceFrom $1,346Free cancellationRating
8.0
659 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,406Free cancellationRating
7.4
10,058 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Sydney to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Sydney to Chicago . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Sydney to Chicago with flexible booking policies on momondo?

Flights from Sydney to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Sydney to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Sydney to Chicago.

I’m not ready to book a flight from Sydney to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Sydney and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport