How long is the flight from Sydney to Chicago?

For as low as $1,201, American Airlines can have you in Chicago from Sydney in 19h 35m. The distance from Sydney to Chicago is about 9228 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What is the cheapest airline to fly from Sydney to Chicago round-trip?

According to our current data, Qantas Airways ($631), offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 35% less than the average price by searching for this airline.

What are the cheapest airlines to fly from Sydney to Chicago one-way?

The cheapest airlines for a one-way flight from Sydney to Chicago are Qantas Airways ($408), American Airlines ($469), and Air Canada ($530).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Sydney to Chicago as you normally would.

Most accurate provider : When it comes to deals on Sydney-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sydney-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Sydney-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Sydney-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sydney-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago. You should not have trouble finding flights to Chicago from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Sydney airport to Chicago. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.

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

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

How can I find direct flights from Sydney to Chicago?

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

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

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

$622+ Flights from Sydney to Chicago

Q: How much does it cost to fly round-trip from Sydney to Chicago?

Airfare is below average for this route at the moment. Sydney to Chicago flights typically cost between $1,179 and $1,677 in January. The cheapest round-trip price found within the last 3 days was $1,069 on Air New Zealand (Jan 28-Feb 4).

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Find cheap flights from Sydney to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 52 days in advance, depart on a Thursday or Sunday and return on a Saturday

Cheap flight deals from Sydney to Chicago

Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Thu 12/2511:50 amSYD - ORD

1 stop22h 15mUnited Airlines

Wed 1/212:40 pmORD - SYD

1 stop22h 40mUnited Airlines

Deal found 12/16

$1,149

Tue 12/1612:10 pmSYD - ORD

1 stop33h 50mUnited Airlines

Mon 1/121:00 pmORD - SYD

2 stops24h 20mUnited Airlines

Deal found 12/14

$1,151

Thu 12/1811:50 amSYD - ORD

1 stop19h 50mUnited Airlines

Sat 1/310:10 pmORD - SYD

1 stop39h 10mUnited Airlines

Deal found 12/15

$1,155

Wed 12/1711:50 amSYD - ORD

1 stop19h 51mUnited Airlines

Thu 1/2211:05 amORD - SYD

1 stop29h 10mUnited Airlines

Deal found 12/15

$1,197

Thu 12/2511:50 amSYD - ORD

1 stop19h 50mUnited Airlines

Fri 1/237:58 pmORD - SYD

1 stop44h 17mUnited Airlines

Deal found 12/16

$1,199

Sat 12/202:00 pmSYD - ORD

2 stops27h 14mUnited Airlines

Sat 1/109:01 amORD - SYD

2 stops28h 19mUnited Airlines

Deal found 12/16

$1,249

Tue 12/2311:20 amSYD - ORD

1 stop26h 05mVirgin Australia

Tue 1/1312:45 pmORD - SYD

1 stop24h 35mVirgin Australia

Deal found 12/15

$1,351

Sat 12/2011:20 amSYD - ORD

1 stop34h 17mVirgin Australia

Sat 1/108:10 pmORD - SYD

1 stop43h 55mVirgin Australia

Deal found 12/16

$1,374

Thu 12/2512:10 pmSYD - ORD

2 stops23h 35mUnited Airlines

Fri 1/163:53 pmORD - SYD

1 stop22h 07mUnited Airlines

Deal found 12/16

$1,462

Tue 12/162:00 pmSYD - ORD

2 stops23h 25mUnited Airlines

Wed 1/146:29 pmORD - SYD

1 stop21h 46mUnited Airlines

Deal found 12/14

$1,626

Thu 12/252:15 pmSYD - MDW

2 stops25h 07mDelta

Wed 1/2110:46 amMDW - SYD

2 stops28h 44mDelta

Deal found 12/16

$1,676

Thu 12/2510:40 amSYD - MDW

2 stops28h 42mDelta

Fri 1/231:26 pmMDW - SYD

2 stops26h 04mDelta

Deal found 12/16

$1,726

Best flights from Sydney to Chicago
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 16, 2025.

Tue 3/311:20 amSYD - ORD

1 stop23h 16mAmerican Airlines

Tue 4/145:30 pmORD - SYD

1 stop22h 35mAmerican Airlines

Deal found 12/16

$1,142

Sat 5/1611:55 amSYD - ORD

2 stops24h 36mAir New Zealand

Sat 6/64:40 pmORD - SYD

2 stops25h 05mAir New Zealand

Deal found 12/16

$1,173

Sat 5/1611:55 amSYD - ORD

2 stops26h 33mMultiple Airlines

Sat 6/64:40 pmORD - SYD

2 stops25h 05mMultiple Airlines

Deal found 12/15

$1,175

Thu 2/1912:10 pmSYD - ORD

1 stop19h 35mUnited Airlines

Fri 3/62:26 pmORD - SYD

2 stops25h 39mUnited Airlines

Deal found 12/15

$1,201

Thu 6/1111:50 amSYD - ORD

2 stops32h 15mANA

Thu 8/65:45 pmORD - SYD

1 stop24h 40mANA

Deal found 12/16

$1,216

Tue 3/311:20 amSYD - ORD

2 stops37h 40mAir Canada

Tue 4/147:10 amORD - SYD

3 stops33h 10mAir Canada

Deal found 12/16

$1,359

Sat 5/169:10 amSYD - ORD

1 stop21h 46mQantas Airways

Sat 6/66:45 pmORD - SYD

1 stop21h 20mQantas Airways

Deal found 12/15

$1,387

Fri 6/129:15 amSYD - ORD

1 stop29h 30mDelta

Sun 7/127:00 amORD - SYD

1 stop32h 35mDelta

Deal found 12/16

$1,427

Fri 2/202:00 pmSYD - ORD

2 stops25h 52mUnited Airlines

Fri 3/66:20 pmORD - SYD

1 stop21h 45mUnited Airlines

Deal found 12/15

$1,251

Fri 2/611:20 amSYD - ORD

1 stop20h 21mAir Canada

Fri 2/132:00 pmORD - SYD

2 stops26h 35mAir Canada

Deal found 12/14

$1,375

Thu 1/298:15 pmSYD - ORD

3 stops35h 26mMultiple Airlines

Thu 2/58:43 pmORD - SYD

3 stops41h 42mMultiple Airlines

Deal found 12/14

$1,422

Thu 2/1910:40 amSYD - MDW

2 stops29h 02mDelta

Fri 3/61:28 pmMDW - SYD

2 stops26h 02mDelta

Deal found 12/15

$1,429

Fri 2/2010:40 amSYD - MDW

2 stops24h 05mDelta

Fri 3/61:28 pmMDW - SYD

2 stops26h 02mDelta

Deal found 12/15

$1,479

Tue 1/1310:40 amSYD - MDW

2 stops24h 52mDelta

Tue 1/2010:48 amMDW - SYD

2 stops27h 02mDelta

Deal found 12/15

$1,579

Thu 1/2910:40 amSYD - MDW

2 stops23h 49mDelta

Thu 2/512:48 pmMDW - SYD

2 stops25h 02mDelta

Deal found 12/14

$1,628

Fri 1/3010:40 amSYD - MDW

2 stops24h 15mDelta

Fri 2/61:26 pmMDW - SYD

2 stops26h 04mDelta

Deal found 12/16

$1,676

Fri 6/129:15 amSYD - MDW

2 stops24h 16mDelta

Sun 7/129:30 amMDW - SYD

2 stops30h 05mDelta

Deal found 12/15

$1,780

Fri 5/297:55 amSYD - MDW

2 stops43h 35mMultiple Airlines

Fri 6/59:20 amMDW - SYD

2 stops30h 00mMultiple Airlines

Deal found 12/15

$11,219

Thu 5/289:15 amSYD - MDW

2 stops24h 16mDelta

Fri 6/51:05 pmMDW - SYD

2 stops26h 30mDelta

Deal found 12/15

$7,903

Wed 1/710:40 amSYD - MDW

2 stops22h 49mDelta

Mon 4/279:30 amMDW - SYD

2 stops30h 05mDelta

Deal found 12/15

$11,017

Sun 1/1110:40 amSYD - MDW

2 stops23h 57mDelta

Thu 1/229:32 amMDW - SYD

2 stops28h 18mDelta

Deal found 12/16

$12,734

Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated December 16, 2025 and is based on user searches.

Tue 12/1612:10 pmSYD - ORD

1 stop33h 50mUnited Airlines

Mon 1/121:00 pmORD - SYD

2 stops24h 20mUnited Airlines

Deal found 12/14

$1,151

Wed 12/1711:50 amSYD - ORD

1 stop19h 51mUnited Airlines

Thu 1/2211:05 amORD - SYD

1 stop29h 10mUnited Airlines

Deal found 12/15

$1,197

Thu 12/1811:50 amSYD - ORD

1 stop19h 50mUnited Airlines

Sat 1/310:10 pmORD - SYD

1 stop39h 10mUnited Airlines

Deal found 12/15

$1,155

Sat 12/202:00 pmSYD - ORD

2 stops27h 14mUnited Airlines

Sat 1/109:01 amORD - SYD

2 stops28h 19mUnited Airlines

Deal found 12/16

$1,249

Sat 12/2011:20 amSYD - ORD

1 stop34h 17mVirgin Australia

Sat 1/108:10 pmORD - SYD

1 stop43h 55mVirgin Australia

Deal found 12/16

$1,374

Tue 12/2311:20 amSYD - ORD

1 stop26h 05mVirgin Australia

Tue 1/1312:45 pmORD - SYD

1 stop24h 35mVirgin Australia

Deal found 12/15

$1,351

Thu 12/252:00 pmSYD - ORD

2 stops21h 55mUnited Airlines

Wed 1/211:00 pmORD - SYD

2 stops24h 20mUnited Airlines

Deal found 12/16

$1,149

Thu 12/2512:10 pmSYD - ORD

2 stops21h 49mUnited Airlines

Fri 1/239:05 pmORD - SYD

1 stop43h 00mUnited Airlines

Deal found 12/16

$1,199

Tue 1/1310:40 amSYD - MDW

2 stops24h 52mDelta

Tue 1/2010:48 amMDW - SYD

2 stops27h 02mDelta

Deal found 12/15

$1,579

Thu 1/291:55 pmSYD - ORD

2 stops23h 30mAir New Zealand

Thu 2/53:53 pmORD - SYD

2 stops25h 37mAir New Zealand

Deal found 12/14

$1,235

Thu 1/2911:20 amSYD - ORD

1 stop20h 21mAir Canada

Thu 2/53:35 pmORD - SYD

1 stop25h 00mAir Canada

Deal found 12/14

$1,361

Fri 1/309:55 amSYD - ORD

2 stops26h 55mAir New Zealand

Fri 2/63:53 pmORD - SYD

2 stops23h 52mAir New Zealand

Deal found 12/16

$1,139

One-way flights from Sydney to Chicago
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated December 16, 2025.

Tue 2/106:25 pmSYD - ORD

3 stops58h 36mMultiple Airlines

Deal found 12/15

$622

Tue 2/109:55 amSYD - ORD

2 stops25h 57mAir New Zealand

Deal found 12/15

$651

Sat 2/78:30 amSYD - ORD

3 stops56h 20mMultiple Airlines

Deal found 12/15

$669

Sat 2/71:55 pmSYD - ORD

2 stops23h 30mAir New Zealand

Deal found 12/15

$703

Tue 2/1011:20 amSYD - ORD

1 stop20h 21mAir Canada

Deal found 12/15

$770

Sat 6/131:15 pmSYD - ORD

3 stops31h 16mMultiple Airlines

Deal found 12/15

$812

Sun 6/1412:15 pmSYD - ORD

2 stops47h 45mMultiple Airlines

Deal found 12/15

$824

Sat 2/711:20 amSYD - ORD

2 stops37h 45mAir Canada

Deal found 12/15

$856

Tue 2/1011:20 amSYD - ORD

1 stop22h 29mQantas Airways

Deal found 12/16

$864

Tue 12/237:15 amSYD - MDW

3 stops43h 06mMultiple Airlines

Deal found 12/16

$1,289

Tue 12/2310:40 amSYD - MDW

2 stops22h 40mDelta

Deal found 12/16

$1,347

Sat 1/39:40 amSYD - MDW

3 stops45h 19mMultiple Airlines

Deal found 12/15

$2,123

Find flight deals from Sydney to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$1,069 (BYOjet)
One-way from	$622 (Kiwi.com)
Popular in	December
Cheapest in	March
Average price	$1,463

Provider with most accurate pricing for Sydney Kingsford Smith-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago (CHI) flights.

Search Deals

From Sydney Kingsford Smith to Chicago (CHI)

Search Deals

One-way flight from Sydney Kingsford Smith to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 20% potential increase in price ($258 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($44 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

11:20 am-5:36 pm

1 stop23h 16m

Chicago O'Hare Intl

Tue 4/14

5:30 pm-7:05 am

1 stop22h 35m

$1,142

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 5/16

11:55 am-9:31 pm

2 stops24h 36m

Chicago O'Hare Intl

Sat 6/6

4:40 pm-8:45 am

2 stops25h 05m

$1,173

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 5/16

11:55 am-11:28 pm

2 stops26h 33m

Chicago O'Hare Intl

Sat 6/6

4:40 pm-8:45 am

2 stops25h 05m

$1,175

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 2/19

12:10 pm-2:45 pm

1 stop19h 35m

Chicago O'Hare Intl

Fri 3/6

2:26 pm-9:05 am

2 stops25h 39m

$1,201

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 6/11

11:50 am-5:05 am

2 stops32h 15m

Chicago O'Hare Intl

Thu 8/6

5:45 pm-9:25 am

1 stop24h 40m

$1,216

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 2/20

2:00 pm-10:52 pm

2 stops25h 52m

Chicago O'Hare Intl

Fri 3/6

6:20 pm-9:05 am

1 stop21h 45m

$1,251

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 3/3

11:20 am-8:00 am

2 stops37h 40m

Chicago O'Hare Intl

Tue 4/14

7:10 am-7:20 am

3 stops33h 10m

$1,359

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 2/6

11:20 am-2:41 pm

1 stop20h 21m

Chicago O'Hare Intl

Fri 2/13

2:00 pm-9:35 am

2 stops26h 35m

$1,375

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 5/16

9:10 am-3:56 pm

1 stop21h 46m

Chicago O'Hare Intl

Sat 6/6

6:45 pm-7:05 am

1 stop21h 20m

$1,387

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/29

8:15 pm-2:41 pm

3 stops35h 26m

Chicago O'Hare Intl

Thu 2/5

8:43 pm-7:25 am

3 stops41h 42m

$1,422

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 33 results

Compare providers for flights from Sydney to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sydney to Chicago in December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Sydney-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sydney-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Sydney-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Sydney-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sydney-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.

Estimated round-trip 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 Sydney to Chicago

How far ahead should I book a flight from Sydney to Chicago?

The best time to book flights from Sydney to Chicago is 52 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $620). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,026). 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.

How much does it cost to fly round-trip from Sydney to Chicago?

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

Los Angeles (LAX) – chosen by Cheapflights users on 86% of 1-stop itineraries from Sydney to Chicago on Cheapflights.

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

Los Angeles (LAX) is the most affordable 1-stop option, with an average round-trip price of $1,065.

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

Flights via Los Angeles (LAX) have the shortest average one-way travel time for 1-stop routes: 20h 23m.

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

Flights via Los Angeles (LAX) offer the fastest connection on this route, with an average layover time of 2h 15m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Qantas Airways

7.5

Good

946 reviews

Reviews

1 / 20

6.0

Good

Marco,Dec 2025

BOS - LAX

There was no WiFi or tv traveling from LAX to Sydney. Way too long of a flight to have nothing.

Qantas Airways

7.5

Good

946 reviews

Qantas Airways

7.5

Good

946 reviews

Reviews

1 / 20

6.0

Good

Marco,Dec 2025

BOS - LAX

There was no WiFi or tv traveling from LAX to Sydney. Way too long of a flight to have nothing.

United Airlines

7.4

Good

9,094 reviews

Qantas Airways

7.5

Good

946 reviews

Reviews

1 / 20

6.0

Good

Marco,Dec 2025

BOS - LAX

There was no WiFi or tv traveling from LAX to Sydney. Way too long of a flight to have nothing.

Related info for your journey

What airport do you fly from for flights from Sydney to Chicago?
Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago. You should not have trouble finding flights to Chicago from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Sydney airport to Chicago. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.
How long is the flight from Sydney to Chicago?
For as low as $1,201, American Airlines can have you in Chicago from Sydney in 19h 35m. The distance from Sydney to Chicago is about 9228 mi. Both multi-stop and nonstop flights can be found to your destination and back.
What is the cheapest airline to fly from Sydney to Chicago round-trip?
According to our current data, Qantas Airways ($631), offers the cheapest pricing from Sydney to Chicago. You may be able to fly from Sydney to Chicago for 35% less than the average price by searching for this airline.
What are the cheapest airlines to fly from Sydney to Chicago one-way?
The cheapest airlines for a one-way flight from Sydney to Chicago are Qantas Airways ($408), American Airlines ($469), and Air Canada ($530).
Can I find deals for flights from Sydney to Chicago that include hotel bookings?
Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Sydney to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.
Can I find deals for business class flights from Sydney to Chicago?
Yes. Cheapflights offers flight deals from Sydney to Chicago 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 Sydney to Chicago?
Currently, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $620). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,026). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

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Top airline flying from Sydney to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Qantas Airways	Cheapest$631	Average$762	FlexibilityNo cancel fee	On-time74%

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$622+ Cheap flights from Sydney (SYD) to Chicago (CHI)

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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Sydney to Chicago with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 52 days in advance, depart on a Thursday or Sunday and return on a Saturday

Cheap flight deals from Sydney to Chicago

Cheapest flights from Sydney to ChicagoExplore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Find flight deals from Sydney to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

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

Compare providers for flights from Sydney to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sydney to Chicago in December.

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.

Cheapflights Insights

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

How far ahead should I book a flight from Sydney to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Sydney to Chicago. Price data was last updated on December 12, 2025.

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

How much does it cost to fly round-trip from Sydney to Chicago?

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

Share of 1-stop round-trip flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

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

Average round-trip fare for 1-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

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

Shortest average travel time for 1-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

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

Average layover duration for 1-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Sydney to Chicago. 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 from for flights from Sydney to Chicago?

How long is the flight from Sydney to Chicago?

What is the cheapest airline to fly from Sydney to Chicago round-trip?

What are the cheapest airlines to fly from Sydney to Chicago one-way?

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

How can I find direct flights from Sydney to Chicago?

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

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

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Alternative routes for Sydney to Chicago

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Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.