Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Sydney to Chicago from $500

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 10/31. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize 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 round-trip flights

Enter your travel dates to find the best prices.
Air New Zealand Logo
1:55 pm - 10:59 pmSYD-ORD
26h 04m2 stops
Air New Zealand Logo
10:35 am - 8:45 amORD-SYD
29h 10m2 stops
$941Air New Zealand
Find Deal
lun., nov. 3 - jue., nov. 13
Air New Zealand Logo
11:50 am - 11:15 pmSYD-ORD
27h 25m2 stops
Air New Zealand Logo
3:40 pm - 10:30 amORD-SYD
26h 50m2 stops
$977Air New Zealand
Find Deal
mié., oct. 15 - mar., oct. 28
Air Canada Logo
11:20 am - 2:41 pmSYD-ORD
20h 21m1 stop
Air Canada Logo
3:40 pm - 9:35 amORD-SYD
24h 55m1 stop
$1,098Air Canada
Find Deal
mar., nov. 11 - mar., nov. 18
Air Canada Logo
10:20 am - 3:00 pmSYD-ORD
20h 40m1 stop
Air Canada Logo
3:40 pm - 8:35 amORD-SYD
24h 55m1 stop
$1,118Air Canada
Find Deal
mar., oct. 14 - lun., oct. 27
Multiple Airlines Logo
8:00 am - 3:00 pmSYD-ORD
23h 00m2 stops
Multiple Airlines Logo
3:40 pm - 12:40 pmORD-SYD
29h 00m2 stops
$1,229Multiple Airlines
Find Deal
lun., oct. 13 - dom., oct. 26
Multiple Airlines Logo
8:00 am - 3:00 pmSYD-ORD
23h 00m2 stops
Multiple Airlines Logo
10:38 am - 9:35 amORD-SYD
29h 57m3 stops
$1,314Multiple Airlines
Find Deal
lun., oct. 20 - mar., nov. 4
United Airlines Logo
12:10 pm - 2:55 pmSYD-ORD
19h 45m1 stop
United Airlines Logo
2:12 pm - 9:05 amORD-SYD
25h 53m2 stops
$1,411United Airlines
Find Deal
mié., dic. 24 - jue., ene. 29
United Airlines Logo
12:10 pm - 8:05 pmSYD-ORD
24h 55m1 stop
United Airlines Logo
2:40 pm - 6:20 amORD-SYD
22h 40m1 stop
$1,412United Airlines
Find Deal
jue., dic. 25 - vie., ene. 23
American Airlines Logo
11:20 am - 4:51 pmSYD-ORD
22h 31m1 stop
American Airlines Logo
7:18 am - 9:00 amORD-SYD
32h 42m1 stop
$1,491American Airlines
Find Deal
jue., dic. 25 - vie., ene. 23
American Airlines Logo
11:20 am - 5:28 pmSYD-ORD
23h 08m2 stops
American Airlines Logo
9:02 am - 9:00 amORD-SYD
30h 58m1 stop
$1,497American Airlines
Find Deal
jue., dic. 25 - vie., ene. 23

Air New Zealand flights from Sydney to Chicago

Our best Air New Zealand deals on Sydney to Chicago flight tickets
Air New Zealand
Nov 3
SYD1:55 pmSydney Kingsford Smith
26h 04m
2 stops
ORD10:59 pmChicago O'Hare Intl
Nov 13
ORD10:35 amChicago O'Hare Intl
29h 10m
2 stops
SYD8:45 amSydney Kingsford Smith
$941
Find similar
Air New Zealand
Oct 15
SYD11:50 amSydney Kingsford Smith
27h 25m
2 stops
ORD11:15 pmChicago O'Hare Intl
Oct 28
ORD3:40 pmChicago O'Hare Intl
26h 50m
2 stops
SYD10:30 amSydney Kingsford Smith
$977
Find similar
Air New Zealand
Oct 14
SYD11:50 amSydney Kingsford Smith
27h 25m
2 stops
ORD11:15 pmChicago O'Hare Intl
Oct 27
ORD2:30 pmChicago O'Hare Intl
28h 00m
2 stops
SYD10:30 amSydney Kingsford Smith
$1,001
Find similar

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
Oct 21
SYD9:45 pmSydney Kingsford Smith
48h 25m
2 stops
ORD6:10 amChicago O'Hare Intl
Nov 5
ORD4:25 pmChicago O'Hare Intl
34h 50m
1 stop
SYD8:15 pmSydney Kingsford Smith
$1,281
Find similar
ANA
Oct 20
SYD9:45 pmSydney Kingsford Smith
61h 50m
2 stops
ORD7:35 pmChicago O'Hare Intl
Nov 4
ORD4:25 pmChicago O'Hare Intl
34h 50m
1 stop
SYD8:15 pmSydney Kingsford Smith
$1,298
Find similar
ANA
Oct 19
SYD9:45 pmSydney Kingsford Smith
47h 21m
2 stops
ORD5:06 amChicago O'Hare Intl
Nov 3
ORD4:25 pmChicago O'Hare Intl
34h 50m
1 stop
SYD8:15 pmSydney Kingsford Smith
$1,316
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 octubre 1, 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

lun. 11/3

1:55 pm-10:59 pm

2 stops26h 04m

Chicago O'Hare Intl

jue. 11/13

10:35 am-8:45 am

2 stops29h 10m

$941

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 10/15

11:50 am-11:15 pm

2 stops27h 25m

Chicago O'Hare Intl

mar. 10/28

3:40 pm-10:30 am

2 stops26h 50m

$977

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mar. 11/11

11:20 am-2:41 pm

1 stop20h 21m

Chicago O'Hare Intl

mar. 11/18

3:40 pm-9:35 am

1 stop24h 55m

$1,098

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mar. 10/14

10:20 am-3:00 pm

1 stop20h 40m

Chicago O'Hare Intl

lun. 10/27

3:40 pm-8:35 am

1 stop24h 55m

$1,118

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

lun. 10/13

8:00 am-3:00 pm

2 stops23h 00m

Chicago O'Hare Intl

dom. 10/26

3:40 pm-12:40 pm

2 stops29h 00m

$1,229

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

lun. 10/20

8:00 am-3:00 pm

2 stops23h 00m

Chicago O'Hare Intl

mar. 11/4

10:38 am-9:35 am

3 stops29h 57m

$1,314

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mié. 12/24

12:10 pm-2:55 pm

1 stop19h 45m

Chicago O'Hare Intl

jue. 1/29

2:12 pm-9:05 am

2 stops25h 53m

$1,411

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

jue. 12/25

12:10 pm-8:05 pm

1 stop24h 55m

Chicago O'Hare Intl

vie. 1/23

2:40 pm-6:20 am

1 stop22h 40m

$1,412

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

jue. 12/25

11:20 am-4:51 pm

1 stop22h 31m

Chicago O'Hare Intl

vie. 1/23

7:18 am-9:00 am

1 stop32h 42m

$1,491

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

jue. 12/25

11:20 am-5:28 pm

2 stops23h 08m

Chicago O'Hare Intl

vie. 1/23

9:02 am-9:00 am

1 stop30h 58m

$1,497

Flights are sorted by cheapest round-trip 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 typical price of a round-trip flight between Sydney and Chicago?

What is the cheapest month to fly to Chicago?

The month of March 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 March, then February is your next best option. Flight prices from Sydney to Chicago during February average around $744.

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 $986 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 October 2025, prices for Sydney to Chicago flights are approximately 60% 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

Direct flights

None
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?

    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 45m.

  • 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
7.6
910 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize 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
vie. 10/31
vie. 11/7
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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport