Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Sydney to Chicago from $690

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 15/4. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Sydney to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Air New Zealand Logo
11:45 - 20:23
SYD
-
ORD
24h 38m
2 stops
Air New Zealand Logo
14:30 - 18:10
ORD
-
SYD
36h 40m
2 stops
$1,453Air New Zealand
Wed, 18 Mar - Wed, 20 May
Air New Zealand Logo
09:55 - 23:58
SYD
-
ORD
31h 03m
2 stops
Air New Zealand Logo
07:00 - 08:45
ORD
-
SYD
33h 45m
2 stops
$1,492Air New Zealand
Sun, 8 Mar - Sun, 15 Mar
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,494Air Canada
Thu, 19 Feb - Thu, 26 Feb
Air Canada Logo
11:20 - 19:45
SYD
-
ORD
25h 25m
2 stops
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m
1 stop
$1,502Air Canada
Thu, 19 Feb - Thu, 26 Feb
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
08:45 - 07:20
ORD
-
SYD
31h 35m
2 stops
$1,505Air Canada
Wed, 18 Feb - Wed, 6 May
Air Canada Logo
11:20 - 16:42
SYD
-
ORD
22h 22m
1 stop
Air Canada Logo
07:15 - 09:35
ORD
-
SYD
33h 20m
2 stops
$1,511Air Canada
Wed, 11 Feb - Thu, 26 Feb
Air Canada Logo
11:20 - 20:10
SYD
-
ORD
25h 50m
2 stops
Air Canada Logo
07:15 - 09:35
ORD
-
SYD
33h 20m
2 stops
$1,516Air Canada
Wed, 11 Feb - Thu, 26 Feb
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
14:00 - 06:35
MDW
-
SYD
25h 35m
2 stops
$1,714Delta
Mon, 16 Mar - Sun, 17 May
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
13:00 - 06:35
MDW
-
SYD
26h 35m
2 stops
$1,787Delta
Thu, 19 Mar - Thu, 21 May
Multiple Airlines Logo
11:20 - 23:51
SYD
-
MDW
29h 31m
2 stops
Multiple Airlines Logo
06:00 - 09:00
MDW
-
SYD
35h 00m
2 stops
$2,017Multiple Airlines
Thu, 5 Mar - Thu, 12 Mar

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
16 Feb
SYD12:25Sydney Kingsford Smith
35h 55m
1 stop
ORD07:20Chicago O'Hare Intl
2 May
ORD19:49Chicago O'Hare Intl
32h 26m
2 stops
SYD19:15Sydney Kingsford Smith
$1,629
ANA
31 May
SYD11:50Sydney Kingsford Smith
35h 50m
1 stop
ORD08:40Chicago O'Hare Intl
29 June
ORD21:30Chicago O'Hare Intl
30h 45m
2 stops
SYD19:15Sydney Kingsford Smith
$1,630

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets
Air New Zealand
18 Mar
SYD11:45Sydney Kingsford Smith
24h 38m
2 stops
ORD20:23Chicago O'Hare Intl
20 May
ORD14:30Chicago O'Hare Intl
36h 40m
2 stops
SYD18:10Sydney Kingsford Smith
$1,453
Air New Zealand
8 Mar
SYD09:55Sydney Kingsford Smith
31h 03m
2 stops
ORD23:58Chicago O'Hare Intl
15 Mar
ORD07:00Chicago O'Hare Intl
33h 45m
2 stops
SYD08:45Sydney Kingsford Smith
$1,492
Air New Zealand
7 Feb
SYD11:45Sydney Kingsford Smith
25h 40m
2 stops
ORD20:25Chicago O'Hare Intl
27 Feb
ORD12:55Chicago O'Hare Intl
26h 50m
2 stops
SYD08:45Sydney Kingsford Smith
$1,626

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 23 January 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

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 18/3

11:45-20:23

2 stops24h 38m

Chicago O'Hare Intl

Wed 20/5

14:30-18:10

2 stops36h 40m

$1,453

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 8/3

09:55-23:58

2 stops31h 03m

Chicago O'Hare Intl

Sun 15/3

07:00-08:45

2 stops33h 45m

$1,492

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Thu 26/2

15:35-09:35

1 stop25h 00m

$1,494

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/2

11:20-19:45

2 stops25h 25m

Chicago O'Hare Intl

Thu 26/2

15:35-09:35

1 stop25h 00m

$1,502

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 18/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Wed 6/5

08:45-07:20

2 stops31h 35m

$1,505

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/2

11:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Thu 26/2

07:15-09:35

2 stops33h 20m

$1,511

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 11/2

11:20-20:10

2 stops25h 50m

Chicago O'Hare Intl

Thu 26/2

07:15-09:35

2 stops33h 20m

$1,516

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 16/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Sun 17/5

14:00-06:35

2 stops25h 35m

$1,714

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Thu 21/5

13:00-06:35

2 stops26h 35m

$1,787

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/3

11:20-23:51

2 stops29h 31m

Chicago Midway

Thu 12/3

06:00-09:00

2 stops35h 00m

$2,017

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 cheapest month to fly to Chicago?

If you don’t want to visit Chicago in March, then you should wait until May to fly from Sydney, when ticket prices are also cheap, with an average price of $1,108.

How far in advance should I book a flight 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 $1,400 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 $1,118 on momondo.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 65% 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 January 2026, prices for Sydney to Chicago flights are approximately 14% 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

19h 45m

Direct flights

None
The fastest flight from Sydney to Chicago takes 19h 45m
There are no direct flights from Sydney to Chicago. There are no popular flight routes from Sydney to Chicago.
Search flight deals

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

    There are 14866.2 km between Sydney Kingsford Smith and Chicago. 19h 45m 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
Qantas AirwaysPriceFrom $952Free cancellationRating
7.5
974 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $1,144Free cancellationRating
7.2
11,180 reviews
Search American Airlines flights
Air CanadaPriceFrom $1,147Free cancellationRating
7.1
10,649 reviews
Search Air Canada flights
Air New ZealandPriceFrom $1,388Free cancellationRating
8.0
573 reviews
Search Air New Zealand flights
United AirlinesPriceFrom $1,451Free cancellationRating
7.4
9,193 reviews
Search United Airlines flights
ANAPriceFrom $1,541Free cancellationRating
8.4
1,078 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 22/2
Sun 1/3
By creating a price alert you accept our terms of use and privacy policy.

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