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Cheap flights from Sydney to Chicago from $893

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 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap return flights

Enter your travel dates to find the best prices.
Delta Logo
10:15 - 16:50
SYD
-
MDW
22h 35m
2 stops
Delta Logo
12:30 - 08:30
MDW
-
SYD
27h 00m
2 stops
$1,458Delta
Thu, 15 Oct - Tue, 17 Nov
Delta Logo
10:15 - 13:47
SYD
-
ORD
19h 32m
1 stop
Delta Logo
07:30 - 08:30
ORD
-
SYD
32h 00m
2 stops
$1,458Delta
Thu, 15 Oct - Tue, 17 Nov
American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
08:35 - 06:10
ORD
-
SYD
28h 35m
1 stop
$1,490American Airlines
Sat, 31 Oct - Wed, 4 Nov
American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,492American Airlines
Sat, 31 Oct - Wed, 4 Nov
American Airlines Logo
11:15 - 13:09
SYD
-
ORD
41h 54m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,493American Airlines
Sat, 31 Oct - Wed, 4 Nov
Qantas Airways Logo
12:00 - 19:36
SYD
-
ORD
22h 36m
1 stop
Qantas Airways Logo
08:50 - 07:05
ORD
-
SYD
31h 15m
1 stop
$1,507Qantas Airways
Thu, 3 Sep - Thu, 10 Sep
American Airlines Logo
11:15 - 06:01
SYD
-
ORD
34h 46m
1 stop
American Airlines Logo
10:15 - 06:10
ORD
-
SYD
26h 55m
1 stop
$1,508American Airlines
Sat, 31 Oct - Wed, 4 Nov
American Airlines Logo
09:10 - 05:00
SYD
-
ORD
34h 50m
1 stop
American Airlines Logo
14:55 - 06:25
ORD
-
SYD
23h 30m
1 stop
$1,513American Airlines
Thu, 1 Oct - Fri, 9 Oct
Multiple Airlines Logo
13:15 - 11:12
SYD
-
MDW
36h 57m
3 stops
Multiple Airlines Logo
06:00 - 11:50
MDW
-
SYD
38h 50m
3 stops
$1,664Multiple Airlines
Mon, 1 Jun - Wed, 17 Jun
Multiple Airlines Logo
13:15 - 11:04
SYD
-
MDW
36h 49m
3 stops
Multiple Airlines Logo
06:00 - 11:50
MDW
-
SYD
38h 50m
3 stops
$1,697Multiple Airlines
Fri, 19 Jun - Sat, 18 Jul

American Airlines flights from Sydney to Chicago

Our best American Airlines deals on Sydney to Chicago flight tickets
American Airlines
31 Oct
SYD11:15Sydney Kingsford Smith
35h 28m
1 stop
ORD06:43Chicago O'Hare Intl
4 Nov
ORD08:35Chicago O'Hare Intl
28h 35m
1 stop
SYD06:10Sydney Kingsford Smith
$1,484
American Airlines
31 Oct
SYD11:15Sydney Kingsford Smith
34h 46m
1 stop
ORD06:01Chicago O'Hare Intl
4 Nov
ORD08:35Chicago O'Hare Intl
28h 35m
1 stop
SYD06:10Sydney Kingsford Smith
$1,490
American Airlines
31 Oct
SYD11:15Sydney Kingsford Smith
34h 46m
1 stop
ORD06:01Chicago O'Hare Intl
4 Nov
ORD10:15Chicago O'Hare Intl
26h 55m
1 stop
SYD06:10Sydney Kingsford Smith
$1,492

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
3 Sept
SYD12:00Sydney Kingsford Smith
22h 36m
1 stop
ORD19:36Chicago O'Hare Intl
10 Sept
ORD08:50Chicago O'Hare Intl
31h 15m
1 stop
SYD07:05Sydney Kingsford Smith
$1,507
Qantas Airways
2 June
SYD06:00Sydney Kingsford Smith
24h 52m
2 stops
ORD15:52Chicago O'Hare Intl
23 June
ORD17:10Chicago O'Hare Intl
29h 45m
2 stops
SYD13:55Sydney Kingsford Smith
$1,730
Qantas Airways
7 June
SYD14:10Sydney Kingsford Smith
40h 39m
2 stops
ORD15:49Chicago O'Hare Intl
2 July
ORD09:00Chicago O'Hare Intl
44h 30m
2 stops
SYD20:30Sydney Kingsford Smith
$1,742

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 20 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
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 15/10

10:15-16:50

2 stops22h 35m

Chicago Midway

Tue 17/11

12:30-08:30

2 stops27h 00m

$1,458

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 15/10

10:15-13:47

1 stop19h 32m

Chicago O'Hare Intl

Tue 17/11

07:30-08:30

2 stops32h 00m

$1,458

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 31/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Wed 4/11

08:35-06:10

1 stop28h 35m

$1,490

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 31/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Wed 4/11

10:15-06:10

1 stop26h 55m

$1,492

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 31/10

11:15-13:09

1 stop41h 54m

Chicago O'Hare Intl

Wed 4/11

10:15-06:10

1 stop26h 55m

$1,493

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 3/9

12:00-19:36

1 stop22h 36m

Chicago O'Hare Intl

Thu 10/9

08:50-07:05

1 stop31h 15m

$1,507

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 31/10

11:15-06:01

1 stop34h 46m

Chicago O'Hare Intl

Wed 4/11

10:15-06:10

1 stop26h 55m

$1,508

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:10-05:00

1 stop34h 50m

Chicago O'Hare Intl

Fri 9/10

14:55-06:25

1 stop23h 30m

$1,513

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/6

13:15-11:12

3 stops36h 57m

Chicago Midway

Wed 17/6

06:00-11:50

3 stops38h 50m

$1,664

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 19/6

13:15-11:04

3 stops36h 49m

Chicago Midway

Sat 18/7

06:00-11:50

3 stops38h 50m

$1,697

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?

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in December, then you should wait until August to fly from Sydney, when ticket prices are also cheap, with an average price of $881.

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 $1,856 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 $1,386 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 2% 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 May 2026, prices for Sydney to Chicago flights are approximately 9% more expensive 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

19h 32m

Direct flights

None
The fastest flight from Sydney to Chicago takes 19h 32m
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. 19h 32m 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 $1,064Free cancellationRating
7.1
11,065 reviews
Search Air Canada flights
American AirlinesPriceFrom $1,095Free cancellationRating
7.1
11,642 reviews
Search American Airlines flights
Qantas AirwaysPriceFrom $1,239Free cancellationRating
7.5
1,037 reviews
Search Qantas Airways flights
Air New ZealandPriceFrom $1,329Free cancellationRating
8.0
647 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,389Free cancellationRating
7.4
9,736 reviews
Search United Airlines flights
ANAPriceFrom $1,475Free cancellationRating
8.3
1,211 reviews
Search ANA 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