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Cheap flights from Chicago to Sydney from $637

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SYD
30 Nov — 7 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Chicago to Sydney Kingsford Smith are usually found in August or September, booked 2 days in advance, depart on a Sunday or Monday and return on a Tuesday

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Cheapest flights from Chicago to Sydney
Explore the most affordable flight options available from Chicago to Sydney. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 October 2025.

Tue 2/1215:40ORD - SYD
1 stop22h 15mAir Canada
Tue 16/1211:20SYD - ORD
2 stops34h 40mAir Canada
Deal found 30/10$1,290
Thu 11/1215:40ORD - SYD
1 stop22h 15mAir Canada
Thu 25/1216:00SYD - ORD
1 stop39h 41mAir Canada
Deal found 30/10$1,293
Sat 15/1120:18ORD - SYD
2 stops44h 17mMultiple Airlines
Mon 24/1121:20SYD - ORD
2 stops34h 21mMultiple Airlines
Deal found 28/10$1,296
Sun 30/1115:40ORD - SYD
1 stop24h 55mAir Canada
Sun 14/1211:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 30/10$1,297
Sun 16/1120:00ORD - SYD
2 stops44h 35mAir Canada
Tue 16/1211:20SYD - ORD
2 stops41h 09mAir Canada
Deal found 30/10$1,300
Mon 17/1117:55ORD - SYD
3 stops46h 40mAir Canada
Tue 16/1211:20SYD - ORD
2 stops41h 09mAir Canada
Deal found 30/10$1,302
Mon 1/1215:40ORD - SYD
2 stops33h 25mMultiple Airlines
Fri 5/1208:30SYD - ORD
2 stops23h 11mMultiple Airlines
Deal found 30/10$1,311
Sun 7/1215:40ORD - SYD
2 stops33h 25mAir Canada
Sun 14/1211:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 30/10$1,313
Fri 28/1115:40ORD - SYD
1 stop24h 55mAir Canada
Fri 5/1208:30SYD - ORD
2 stops23h 11mAir Canada
Deal found 29/10$1,316
Wed 3/1215:40ORD - SYD
2 stops31h 15mMultiple Airlines
Sat 13/1219:15SYD - ORD
2 stops36h 26mMultiple Airlines
Deal found 29/10$1,323
Thu 13/1109:00MDW - SYD
2 stops31h 00mMultiple Airlines
Thu 20/1117:45SYD - MDW
2 stops37h 55mMultiple Airlines
Deal found 29/10$1,731
Sun 7/1206:15MDW - SYD
2 stops33h 45mMultiple Airlines
Sun 14/1217:45SYD - MDW
2 stops34h 23mMultiple Airlines
Deal found 29/10$1,736

Cheap flight deals from Chicago to Sydney

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sydney (SYD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 31 October 2025.

Round-trip from

$1,290

One-way from

$637

Popular in

December

Cheapest in

August

Average price

$1,381
Air Canada
  • Air Canada
  • 2/12-16/12
  • 3 total stops
  • 56h 55m total
  • Chicago to Sydney
Search Deals
5/12
  • 5/12
  • 2 total stops
  • 43h 15m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($486 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($88 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Chicago to Sydney 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, Cheapflights users made 647,157 searches. Data last updated 31 October 2025.
Use the filters below to find and compare flights from Chicago to Sydney that are best for you.

Fly from

Chicago

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 25/3

15:40-12:40

2 stops29h 00m

Sydney Kingsford Smith

Mon 6/4

09:20-10:57

2 stops40h 37m

$1,409

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 10/11

12:45-07:00

1 stop25h 15m

Sydney Kingsford Smith

Wed 19/11

12:10-14:50

1 stop19h 40m

$1,923

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 21/3

21:05-07:00

1 stop41h 55m

Sydney Kingsford Smith

Sun 29/3

11:20-12:08

1 stop40h 48m

$1,954

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 10/11

18:25-09:15

1 stop21h 50m

Sydney Kingsford Smith

Thu 20/11

12:10-14:50

1 stop19h 40m

$1,999

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 12/11

18:25-09:15

1 stop21h 50m

Sydney Kingsford Smith

Sat 22/11

11:50-14:53

1 stop20h 03m

$1,999

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 15/11

18:25-09:15

1 stop21h 50m

Sydney Kingsford Smith

Wed 19/11

12:10-14:50

1 stop19h 40m

$1,999

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 14/1

09:01-06:20

2 stops28h 19m

Sydney Kingsford Smith

Sat 24/1

12:10-18:48

1 stop23h 38m

$2,007

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 12/1

21:05-09:05

1 stop43h 00m

Sydney Kingsford Smith

Mon 26/1

12:10-16:57

1 stop21h 47m

$2,056

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 14/11

09:41-08:30

2 stops29h 49m

Sydney Kingsford Smith

Sat 22/11

10:40-18:08

2 stops24h 28m

$2,085

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 19/1

14:40-06:20

1 stop22h 40m

Sydney Kingsford Smith

Sat 24/1

12:10-17:04

2 stops21h 54m

$2,104

Flights are sorted by cheapest return flights first.

Deals found on 29/10

Showing 1-10 of 43 results
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Best time to book a flight from Chicago to Sydney

Have a flexible travel schedule? Discover the best time to fly to Sydney from Chicago with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sydney

What is the cheapest month to book a flight from Chicago to Sydney?

Currently, August is the cheapest month in which you can book a flight from Chicago to Sydney (average of $302). Flying from Chicago to Sydney in January is currently the most expensive (average of $1,307). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SYD?

Find hourly flight availability from Chicago to Sydney. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 31 October 2025.

When flying from Chicago to Sydney, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 49% versus a flight at midday.

What’s the top stopover airport for flights from Chicago to Sydney?

Share of one-stop return flights from Chicago to Sydney chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Los Angeles (LAX) – chosen by Cheapflights users on 73% of one-stop itineraries from Chicago to Sydney on Cheapflights.

What’s the cheapest stopover airport for flights from Chicago to Sydney?

Average return fare for one-stop flights from Chicago to Sydney, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Dallas (DFW) is the most affordable one-stop option, with an average return flight price of $1,300.

What’s the fastest stopover option from Chicago to Sydney?

Shortest average travel time for one-stop one-way flights from Chicago to Sydney, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via San Francisco (SFO) have the shortest average one-way travel time for one-stop routes: 21h 18m.

Which airport typically offers the quickest stopover for flights from Chicago to Sydney?

Average stopover duration for one-stop one-way flights from Chicago to Sydney, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Dallas (DFW) offer the fastest connection on this route, with an average stopover time of 1h 10m.

Reviews of airlines servicing Sydney

Get insights into the airlines that provide service to Sydney. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sydney. Reviews last updated 31 October 2025.
Read reviews from past customers who have flown with Qantas Airways from Chicago to Sydney. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
925 reviews
Check prices

Comfort

7.5

Entertainment

7.2

Food

7.0

Overall

7.5

Boarding

7.7

Crew

8.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
Qantas Airways
7.5
Good
925 reviews
Qantas Airways
7.5
Good
925 reviews
Check prices

Comfort

7.5

Entertainment

7.2

Food

7.0

Overall

7.5

Boarding

7.7

Crew

8.2

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sydney. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Sydney from Chicago?

    For a flight from Chicago to Sydney, you will be flying into Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre vof the city. Kingsford Smith is the only Sydney airport and it handles 0 inbound flights from Chicago per day. 2 airlines have flights to Sydney Kingsford Smith from Chicago on a regular basis.

  • How long is the flight from Chicago to Sydney?

    Airlines like Air Canada, United Airlines, and Delta fly from Chicago to Sydney in about 25h 15m. The time it takes to get you to your destination can typically vary by up to 4h 34m. Chicago and Sydney are separated by a distance of 14851 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Sydney round-trip?

    Cheapflights users have booked flights from Chicago to Sydney round-trip from $1,305. Another airline that can offer you cheap pricing is Qantas Airways. American Airlines is currently priced 10% below the average price you’ll pay for this route.

  • Can I find deals for flights from Chicago to Sydney that include hotel bookings?

    Yes. In addition to deals on Chicago to Sydney flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Sydney?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sydney.

  • Can I find deals for business class flights from Chicago to Sydney?

    Yes. Cheapflights offers flight deals from Chicago to Sydney by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Sydney?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Sydney (average of $302). Flying from Chicago to Sydney in January is currently the most expensive (average of $1,307). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Katoomba
Penrith
Manly
Terrigal
Randwick
Lithgow
Coogee
Leura
Bondi Beach
Cronulla

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Sydney

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Sydney flights
Midway to Sydney flights
St. Louis to Sydney flights

Top 2 airlines flying from Chicago to Sydney

Discover the top 2 airlines that operate flights from Chicago to Sydney. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 31 October 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$1,305Average$1,318FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Qantas AirwaysCheapest$1,331Average$1,431FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Sydney?

Deals for Chicago to Sydney flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Sydney?

Cheapflights helps you find that perfect flight to Sydney from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Chicago to Sydney with no change fees?

Yes, we can. To see specific flights from Chicago to Sydney with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Chicago to Sydney become cheaper?

Yes, Cheapflights offers price alerts on Chicago to Sydney flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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