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Cheap flights from Sydney to Chicago from $384

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 10/15. 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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Find the cheapest flights from Sydney to Chicago (SYD-CHI)

Cheap round-trip flights

Logo
9:25 am - 11:06 pmSYD-ORD
28h 41m1 stop
Logo
7:00 am - 6:35 amORD-SYD
32h 35m1 stop
$1,006
Find Deal
Sat, Aug 30 - Sat, Sep 6
Logo
9:30 am - 11:06 pmSYD-ORD
28h 36m1 stop
Logo
7:00 am - 6:55 amORD-SYD
32h 55m2 stops
$1,009
Find Deal
Sat, Aug 30 - Sat, Sep 6
Air New Zealand Logo
11:50 am - 11:14 pmSYD-ORD
26h 24m2 stops
Air New Zealand Logo
4:10 pm - 10:35 amORD-SYD
27h 25m2 stops
$1,090Air New Zealand
Find Deal
Sat, Aug 30 - Sat, Sep 6
Air Canada Logo
10:20 am - 8:11 pmSYD-ORD
25h 51m2 stops
Air Canada Logo
3:45 pm - 8:20 amORD-SYD
24h 35m1 stop
$1,109Air Canada
Find Deal
Wed, Oct 15 - Tue, Oct 21
American Airlines Logo
9:10 am - 5:18 pmSYD-ORD
23h 08m2 stops
American Airlines Logo
5:46 pm - 7:05 amORD-SYD
22h 19m1 stop
$1,131American Airlines
Find Deal
Fri, Sep 5 - Thu, Sep 18
American Airlines Logo
9:10 am - 5:18 pmSYD-ORD
23h 08m2 stops
American Airlines Logo
7:01 pm - 7:05 amORD-SYD
21h 04m1 stop
$1,135American Airlines
Find Deal
Fri, Sep 5 - Thu, Sep 18
Air New Zealand Logo
8:45 am - 9:36 pmSYD-ORD
28h 51m2 stops
Air New Zealand Logo
3:40 pm - 8:45 amORD-SYD
25h 05m2 stops
$1,136Air New Zealand
Find Deal
Wed, Oct 22 - Wed, Oct 29
United Airlines Logo
10:20 am - 6:26 pmSYD-ORD
23h 06m2 stops
United Airlines Logo
9:25 pm - 7:00 amORD-SYD
42h 35m1 stop
$1,147United Airlines
Find Deal
Fri, Sep 12 - Thu, Sep 18
United Airlines Logo
9:30 am - 2:35 pmSYD-ORD
20h 05m1 stop
United Airlines Logo
2:35 pm - 7:00 amORD-SYD
25h 25m1 stop
$1,148United Airlines
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Fri, Sep 5 - Tue, Sep 16
Air Canada Logo
10:20 am - 8:11 pmSYD-ORD
25h 51m2 stops
Air Canada Logo
10:40 am - 8:20 amORD-SYD
29h 40m3 stops
$1,270Air Canada
Find Deal
Wed, Oct 15 - Tue, Oct 21

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
Aug 25
SYD11:50 amSydney Kingsford Smith
32h 11m
2 stops
ORD5:01 amChicago O'Hare Intl
Sep 9
ORD5:45 pmChicago O'Hare Intl
24h 40m
1 stop
SYD9:25 amSydney Kingsford Smith
$1,114
Find similar
ANA
Sep 3
SYD11:50 amSydney Kingsford Smith
32h 10m
2 stops
ORD5:00 amChicago O'Hare Intl
Sep 17
ORD5:45 pmChicago O'Hare Intl
34h 30m
1 stop
SYD7:15 pmSydney Kingsford Smith
$1,133
Find similar
ANA
Oct 28
SYD12:25 pmSydney Kingsford Smith
32h 51m
2 stops
ORD5:16 amChicago O'Hare Intl
Oct 30
ORD5:35 pmChicago O'Hare Intl
34h 40m
1 stop
SYD8:15 pmSydney Kingsford Smith
$1,176
Find similar

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
Oct 15
SYD10:20 amSydney Kingsford Smith
25h 51m
2 stops
ORD8:11 pmChicago O'Hare Intl
Oct 21
ORD3:45 pmChicago O'Hare Intl
24h 35m
1 stop
SYD8:20 amSydney Kingsford Smith
$1,109
Find similar
Air Canada
Oct 15
SYD10:20 amSydney Kingsford Smith
25h 51m
2 stops
ORD8:11 pmChicago O'Hare Intl
Oct 21
ORD10:40 amChicago O'Hare Intl
29h 40m
3 stops
SYD8:20 amSydney Kingsford Smith
$1,270
Find similar
Air Canada
Oct 28
SYD10:20 amSydney Kingsford Smith
20h 21m
1 stop
ORD2:41 pmChicago O'Hare Intl
Oct 30
ORD3:40 pmChicago O'Hare Intl
24h 55m
1 stop
SYD8:35 amSydney Kingsford Smith
$1,312
Find similar

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated August 14, 2025.
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

Sat 8/30

9:25 am-11:06 pm

1 stop28h 41m

Chicago O'Hare Intl

Sat 9/6

7:00 am-6:35 am

1 stop32h 35m

$1,006

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/30

9:30 am-11:06 pm

1 stop28h 36m

Chicago O'Hare Intl

Sat 9/6

7:00 am-6:55 am

2 stops32h 55m

$1,009

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/30

11:50 am-11:14 pm

2 stops26h 24m

Chicago O'Hare Intl

Sat 9/6

4:10 pm-10:35 am

2 stops27h 25m

$1,090

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/15

10:20 am-8:11 pm

2 stops25h 51m

Chicago O'Hare Intl

Tue 10/21

3:45 pm-8:20 am

1 stop24h 35m

$1,109

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/5

9:10 am-5:18 pm

2 stops23h 08m

Chicago O'Hare Intl

Thu 9/18

5:46 pm-7:05 am

1 stop22h 19m

$1,131

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/5

9:10 am-5:18 pm

2 stops23h 08m

Chicago O'Hare Intl

Thu 9/18

7:01 pm-7:05 am

1 stop21h 04m

$1,135

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/22

8:45 am-9:36 pm

2 stops28h 51m

Chicago O'Hare Intl

Wed 10/29

3:40 pm-8:45 am

2 stops25h 05m

$1,136

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/12

10:20 am-6:26 pm

2 stops23h 06m

Chicago O'Hare Intl

Thu 9/18

9:25 pm-7:00 am

1 stop42h 35m

$1,147

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 9/5

9:30 am-2:35 pm

1 stop20h 05m

Chicago O'Hare Intl

Tue 9/16

2:35 pm-7:00 am

1 stop25h 25m

$1,148

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 10/15

10:20 am-8:11 pm

2 stops25h 51m

Chicago O'Hare Intl

Tue 10/21

10:40 am-8:20 am

3 stops29h 40m

$1,270

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

The month of February is, on average, the cheapest month to fly to Chicago from Sydney, with most prices found around $741. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Sydney to Chicago during March average around $745.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $1,103. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Sydney to Chicago for around $1,626.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Sydney to Chicago during this time can be as low as $1,141. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $1,365.

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 $1,022 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sydney for as low as $776 on momondo.

How have Sydney to Chicago flight prices changed over time?

As of August 2025, prices for Sydney to Chicago flights are approximately 57% 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 round-trip 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

Best Price Found

$384

Fastest flight time

19h 34m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Sydney in the past 72 hours is $384. The best round-trip flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,006.
The fastest flight from Sydney to Chicago takes 19h 34m
There are no direct flights from Sydney to Chicago. Popular non-direct routes for this connection are Sydney Kingsford Smith Airport - Chicago Midway Airport and Sydney Kingsford Smith Airport - Chicago O'Hare Intl Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Sydney Kingsford Smith to Chicago by plane?

    A flight from Sydney Kingsford Smith to Chicago will travel around 9237.5 mi. In terms of flight time, this usually takes a little over 19h 34m.

  • 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 refresh daily.

  • 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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 license 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 $631Free CancellationRating
7.5
895 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $884Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sydney to Chicago for you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Sydney with this policy.

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

Once all potential Sydney to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Sydney to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know 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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport