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Cheap flights from Sydney to Chicago from $656

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Sydney to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:15 pm - 12:45 amSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 30m3 stops Nadi Los Angeles Dallas/Fort Worth
Multiple Airlines Logo
10:26 am - 11:50 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 24m3 stops Atlanta Hartsfield-Jackson Los Angeles Nadi
$943Multiple Airlines
Thu, Sep 10 - Fri, Sep 25
Multiple Airlines Logo
6:05 am - 7:02 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
52h 57m3 stops Nadi Los Angeles Orlando
Multiple Airlines Logo
6:30 am - 12:50 pmORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
38h 20m3 stops Denver Intl Los Angeles Nadi
$943Multiple Airlines
Thu, Oct 8 - Wed, Oct 21
Qantas Airways Logo
9:25 pm - 5:00 amSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 35m1 stop San Francisco
Qantas Airways Logo
8:23 am - 7:05 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 42m1 stop Los Angeles
$992Qantas Airways
Sun, Sep 27 - Mon, Sep 28
Multiple Airlines Logo
9:10 am - 12:23 amSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 13m2 stops Los Angeles Denver Intl
Multiple Airlines Logo
6:00 am - 7:05 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 05m2 stops Dallas/Fort Worth Los Angeles
$1,051Multiple Airlines
Tue, Sep 22 - Tue, Sep 29
Multiple Airlines Logo
10:10 am - 11:43 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
29h 33m2 stops Los Angeles Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:15 am - 8:05 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
33h 50m2 stops Atlanta Hartsfield-Jackson Los Angeles
$1,062Multiple Airlines
Thu, Oct 8 - Wed, Oct 21
Qantas Airways Logo
1:00 pm - 7:16 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 16m1 stop Dallas/Fort Worth
Qantas Airways Logo
8:29 am - 9:00 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
32h 31m1 stop Los Angeles
$1,278Qantas Airways
Wed, Oct 14 - Fri, Oct 30
Qantas Airways Logo
1:00 pm - 7:16 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 16m1 stop Dallas/Fort Worth
Qantas Airways Logo
8:30 pm - 7:30 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
43h 00m1 stop Los Angeles
$1,346Qantas Airways
Wed, Oct 7 - Wed, Oct 14
United Airlines Logo
11:20 am - 2:35 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 15m1 stop Los Angeles
United Airlines Logo
11:00 am - 9:05 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 05m1 stop Los Angeles
$1,611United Airlines
Tue, Dec 1 - Tue, Jan 12
United Airlines Logo
11:50 am - 2:36 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
19h 46m1 stop San Francisco
United Airlines Logo
11:00 pm - 9:05 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
41h 05m1 stop Los Angeles
$1,611United Airlines
Wed, Dec 2 - Mon, Jan 11
United Airlines Logo
9:20 am - 11:26 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
31h 06m1 stop Houston George Bush Intcntl
United Airlines Logo
11:00 pm - 9:05 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
41h 05m1 stop Los Angeles
$1,611United Airlines
Mon, Nov 30 - Mon, Jan 11

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Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
Sep 27
SYD9:25 pmSydney Kingsford Smith
22h 35m
1 stop
ORD5:00 amChicago O'Hare Intl
Sep 28
ORD8:23 amChicago O'Hare Intl
31h 42m
1 stop
SYD7:05 amSydney Kingsford Smith
$992
Qantas Airways
Oct 14
SYD1:00 pmSydney Kingsford Smith
22h 16m
1 stop
ORD7:16 pmChicago O'Hare Intl
Oct 30
ORD8:29 amChicago O'Hare Intl
32h 31m
1 stop
SYD9:00 amSydney Kingsford Smith
$1,278
Qantas Airways
Oct 7
SYD1:00 pmSydney Kingsford Smith
22h 16m
1 stop
ORD7:16 pmChicago O'Hare Intl
Oct 14
ORD8:30 pmChicago O'Hare Intl
43h 00m
1 stop
SYD7:30 amSydney Kingsford Smith
$1,346

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets
Air New Zealand
Nov 4
SYD11:50 amSydney Kingsford Smith
27h 10m
2 stops
ORD10:00 pmChicago O'Hare Intl
Nov 9
ORD10:34 amChicago O'Hare Intl
31h 01m
2 stops
SYD10:35 amSydney Kingsford Smith
$1,235
Air New Zealand
Nov 4
SYD11:50 amSydney Kingsford Smith
26h 59m
2 stops
ORD9:49 pmChicago O'Hare Intl
Nov 9
ORD10:34 amChicago O'Hare Intl
31h 01m
2 stops
SYD10:35 amSydney Kingsford Smith
$1,244
Air New Zealand
Oct 14
SYD11:55 amSydney Kingsford Smith
25h 36m
2 stops
ORD9:31 pmChicago O'Hare Intl
Oct 28
ORD3:47 pmChicago O'Hare Intl
34h 28m
2 stops
SYD6:15 pmSydney Kingsford Smith
$1,254

momondo Fare Finder

 
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

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Route

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Price

Cheapest round-trip

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 9/10

1:15 pm-12:45 am

3 stops26h 30m

Chicago O'Hare Intl

Fri 9/25

10:26 am-11:50 am

3 stops34h 24m

$943

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 10/8

6:05 am-7:02 pm

3 stops52h 57m

Chicago O'Hare Intl

Wed 10/21

6:30 am-12:50 pm

3 stops38h 20m

$943

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 9/27

9:25 pm-5:00 am

1 stop22h 35m

Chicago O'Hare Intl

Mon 9/28

8:23 am-7:05 am

1 stop31h 42m

$992

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 9/22

9:10 am-12:23 am

2 stops30h 13m

Chicago O'Hare Intl

Tue 9/29

6:00 am-7:05 am

2 stops34h 05m

$1,051

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 10/8

10:10 am-11:43 pm

2 stops29h 33m

Chicago Midway

Wed 10/21

6:15 am-8:05 am

2 stops33h 50m

$1,062

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 10/14

1:00 pm-7:16 pm

1 stop22h 16m

Chicago O'Hare Intl

Fri 10/30

8:29 am-9:00 am

1 stop32h 31m

$1,278

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 10/7

1:00 pm-7:16 pm

1 stop22h 16m

Chicago O'Hare Intl

Wed 10/14

8:30 pm-7:30 am

1 stop43h 00m

$1,346
Quickest round-trip

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 12/1

11:20 am-2:35 pm

1 stop20h 15m

Chicago O'Hare Intl

Tue 1/12

11:00 am-9:05 am

1 stop29h 05m

$1,611

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 12/2

11:50 am-2:36 pm

1 stop19h 46m

Chicago O'Hare Intl

Mon 1/11

11:00 pm-9:05 am

1 stop41h 05m

$1,611

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 11/30

9:20 am-11:26 pm

1 stop31h 06m

Chicago O'Hare Intl

Mon 1/11

11:00 pm-9:05 am

1 stop41h 05m

$1,611

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?

Prices are currently low for flights on this route.

Typical prices usually range from $946 to $1,428.
The lowest price recently found on this route was $943.

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Sydney, with most prices found around $1,026. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Sydney to Chicago during October average around $1,043.

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 $1,398 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 $875 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 2% 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

$656

Fastest flight time

20h 44m

Direct flights

None
The best one-way flight to Chicago from Sydney in the past 72 hours is $656. The best round-trip flight deal from Sydney to Chicago found on momondo in the last 72 hours is $943.
The fastest flight from Sydney to Chicago takes 20h 44m
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?

    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 20h 44m.

  • 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 $970Free CancellationRating
7.5
1,085 reviews
Search Qantas Airways flights
United AirlinesPriceFrom $1,113Free CancellationRating
7.4
10,125 reviews
Search United 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport