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Cheap flights from Sydney to Chicago from $388

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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Cheap round-trip flights

Air Canada Logo
9:20 am - 9:09 amSYD-ORD
38h 49m2 stops
Air Canada Logo
3:40 pm - 9:40 pmORD-SYD
39h 00m2 stops
$818Air Canada
Find Deal
Mon, Aug 11 - Wed, Aug 20
Air Canada Logo
10:20 am - 3:00 pmSYD-ORD
20h 40m1 stop
Air Canada Logo
7:15 am - 8:35 amORD-SYD
33h 20m2 stops
$841Air Canada
Find Deal
Tue, Oct 21 - Wed, Oct 29
Air Canada Logo
9:20 am - 2:54 pmSYD-ORD
20h 34m1 stop
Air Canada Logo
10:40 am - 7:20 amORD-SYD
29h 40m2 stops
$845Air Canada
Find Deal
Thu, Aug 14 - Thu, Aug 21
Air Canada Logo
10:20 am - 9:51 amSYD-ORD
39h 31m2 stops
Air Canada Logo
2:00 pm - 8:35 amORD-SYD
26h 35m2 stops
$848Air Canada
Find Deal
Tue, Oct 21 - Wed, Oct 29
Air Canada Logo
9:20 am - 7:59 amSYD-ORD
37h 39m2 stops
Air Canada Logo
10:40 am - 7:20 amORD-SYD
29h 40m2 stops
$850Air Canada
Find Deal
Thu, Aug 14 - Thu, Aug 21
Air Canada Logo
10:20 am - 8:11 pmSYD-ORD
25h 51m2 stops
Air Canada Logo
7:15 am - 8:35 amORD-SYD
33h 20m3 stops
$852Air Canada
Find Deal
Tue, Oct 21 - Wed, Oct 29
Air Canada Logo
9:20 am - 9:31 amSYD-ORD
39h 11m2 stops
Air Canada Logo
9:55 am - 7:20 amORD-SYD
30h 25m2 stops
$854Air Canada
Find Deal
Sun, Aug 10 - Tue, Aug 19
Air Canada Logo
9:20 am - 7:59 amSYD-ORD
37h 39m2 stops
Air Canada Logo
10:40 am - 7:20 amORD-SYD
29h 40m3 stops
$856Air Canada
Find Deal
Thu, Aug 14 - Thu, Aug 21
Logo
2:45 pm - 11:04 pmSYD-ORD
24h 19m2 stops
Logo
6:20 am - 12:45 pmORD-SYD
38h 25m2 stops
$867
Find Deal
Sat, Oct 11 - Sun, Oct 12
Logo
1:45 pm - 11:13 pmSYD-ORD
24h 28m2 stops
Logo
7:00 am - 11:45 amORD-SYD
37h 45m2 stops
$905
Find Deal
Sat, Sep 13 - Sat, Sep 20

Air Canada flights from Sydney to Chicago O'Hare Intl Airport

Our best Air Canada deals on Sydney to Chicago O'Hare Intl Airport flight tickets
Air Canada
Aug 7
SYD9:20 amSydney Kingsford Smith
20h 34m
1 stop
ORD2:54 pmChicago O'Hare Intl
Aug 20
ORD10:40 amChicago O'Hare Intl
29h 40m
2 stops
SYD7:20 amSydney Kingsford Smith
$803
Find similar
Air Canada
Aug 7
SYD9:20 amSydney Kingsford Smith
49h 56m
2 stops
ORD8:16 pmChicago O'Hare Intl
Aug 20
ORD8:55 amChicago O'Hare Intl
31h 25m
2 stops
SYD7:20 amSydney Kingsford Smith
$809
Find similar
Air Canada
Aug 11
SYD9:20 amSydney Kingsford Smith
38h 49m
2 stops
ORD9:09 amChicago O'Hare Intl
Aug 20
ORD3:40 pmChicago O'Hare Intl
39h 00m
2 stops
SYD9:40 pmSydney Kingsford Smith
$818
Find similar

American Airlines flights from Sydney to Chicago O'Hare Intl Airport

Our best American Airlines deals on Sydney to Chicago O'Hare Intl Airport flight tickets
American Airlines
Aug 13
SYD9:10 amSydney Kingsford Smith
23h 00m
2 stops
ORD5:10 pmChicago O'Hare Intl
Sep 3
ORD3:08 pmChicago O'Hare Intl
24h 57m
2 stops
SYD7:05 amSydney Kingsford Smith
$1,034
Find similar
American Airlines
Aug 4
SYD9:10 amSydney Kingsford Smith
22h 52m
1 stop
ORD5:02 pmChicago O'Hare Intl
Aug 25
ORD8:20 amChicago O'Hare Intl
31h 35m
1 stop
SYD6:55 amSydney Kingsford Smith
$1,036
Find similar
American Airlines
Aug 13
SYD9:10 amSydney Kingsford Smith
23h 00m
2 stops
ORD5:10 pmChicago O'Hare Intl
Sep 3
ORD3:08 pmChicago O'Hare Intl
24h 57m
2 stops
SYD7:05 amSydney Kingsford Smith
$1,037
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Sydney to Chicago O'Hare Intl Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Sydney to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 8/11

9:20 am-9:09 am

2 stops38h 49m

Chicago O'Hare Intl

Wed 8/20

3:40 pm-9:40 pm

2 stops39h 00m

$818

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/21

10:20 am-3:00 pm

1 stop20h 40m

Chicago O'Hare Intl

Wed 10/29

7:15 am-8:35 am

2 stops33h 20m

$841

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 8/14

9:20 am-2:54 pm

1 stop20h 34m

Chicago O'Hare Intl

Thu 8/21

10:40 am-7:20 am

2 stops29h 40m

$845

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/21

10:20 am-9:51 am

2 stops39h 31m

Chicago O'Hare Intl

Wed 10/29

2:00 pm-8:35 am

2 stops26h 35m

$848

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 8/14

9:20 am-7:59 am

2 stops37h 39m

Chicago O'Hare Intl

Thu 8/21

10:40 am-7:20 am

2 stops29h 40m

$850

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 10/21

10:20 am-8:11 pm

2 stops25h 51m

Chicago O'Hare Intl

Wed 10/29

7:15 am-8:35 am

3 stops33h 20m

$852

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 8/10

9:20 am-9:31 am

2 stops39h 11m

Chicago O'Hare Intl

Tue 8/19

9:55 am-7:20 am

2 stops30h 25m

$854

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 8/14

9:20 am-7:59 am

2 stops37h 39m

Chicago O'Hare Intl

Thu 8/21

10:40 am-7:20 am

3 stops29h 40m

$856

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 10/11

2:45 pm-11:04 pm

2 stops24h 19m

Chicago O'Hare Intl

Sun 10/12

6:20 am-12:45 pm

2 stops38h 25m

$867

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 9/13

1:45 pm-11:13 pm

2 stops24h 28m

Chicago O'Hare Intl

Sat 9/20

7:00 am-11:45 am

2 stops37h 45m

$905

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Sydney averaging around $746.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Monday when prices can be found for as low as $886. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Sydney because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,619.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Sydney in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $1,274 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $1,432. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Sydney when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $1,032 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Sydney for as low as $840 on momondo.

How have Sydney to Chicago O'Hare Intl Airport flight prices changed over time?

As of July 2025, prices for Sydney to Chicago O'Hare Intl Airport flights are approximately 51% cheaper when compared to flights at the same time last year.

When to book flights from Sydney to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sydney to Chicago O'Hare Intl Airport (SYD to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago O'Hare Intl Airport

Best Price Found

$388

Fastest flight time

19h 34m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Sydney in the past 72 hours is $388. The best round-trip flight deal from Sydney to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $818.
The fastest flight from Sydney to Chicago O'Hare Intl Airport takes 19h 34m
There are no direct flights from Sydney to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Sydney Kingsford Smith Airport - Chicago O'Hare Intl Airport.
Search flight deals

  • How far is Sydney Kingsford Smith to Chicago O'Hare Intl by plane?

    A flight from Sydney Kingsford Smith to Chicago O'Hare Intl will travel around 9224.8 mi. 20h 21m is a normal flight duration for this route.

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

    Prices for flights from Sydney Kingsford Smith Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

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

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Sydney to Chicago O'Hare Intl Airport?

Best airlines flying from Sydney to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Sydney to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Qantas AirwaysPriceFrom $631Free CancellationRating
7.5
887 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
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

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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