How long is the flight from Sydney to Chicago?

Airlines like Air New Zealand, American Airlines, and United Airlines fly from Sydney to Chicago in about 23h 07m. The time it takes to get you to your destination can typically vary by up to 8h 13m. The distance between Sydney and Chicago is about 14851 km. Both multi-stop and direct flights can be found to your destination and back.

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

Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,002. Other airlines that can offer you cheap pricing are American Airlines, from $1,187, and Air Canada, from $1,201. You may be able to fly from Sydney to Chicago for 35% less than the average price by searching for these airlines.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

What are the most popular airlines that fly from Sydney to Chicago?

When booking a flight from Sydney to Chicago, you may want to consider flying on American Airlines, Air Canada or ANA as they are the most popular for this route.

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

For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.

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 holiday 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.

$685+ Flights from Sydney to Chicago

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 82 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Sydney to Chicago

Round-trip from	$1,434
One-way from	$685
Popular in	December
Cheapest in	March
Average price	$1,757

Air New Zealand
24/10-31/10
4 total stops
54h 57m total
Sydney to Chicago

Search Deals

15/10
2 total stops
27h 41m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 22% potential increase in price ($683 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($109 potential savings vs. average return price).

Search Deals

Average for round-trip flights in September 2025

Search Deals

Find 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 26 September 2025.

Thu 6/1109:55SYD - ORD

2 stops31h 20mAir New Zealand

Mon 10/1113:00ORD - SYD

2 stops28h 30mAir New Zealand

Deal found 24/9$1,441

Sun 9/1114:00SYD - ORD

2 stops26h 00mMultiple Airlines

Sun 16/1106:30ORD - SYD

2 stops37h 00mMultiple Airlines

Deal found 25/9$1,510

Sat 8/1111:45SYD - ORD

2 stops25h 40mAir New Zealand

Sat 15/1113:00ORD - SYD

2 stops28h 30mAir New Zealand

Deal found 23/9$1,521

Wed 3/1211:45SYD - ORD

2 stops24h 59mAir New Zealand

Mon 8/1214:35ORD - SYD

2 stops26h 55mAir New Zealand

Deal found 24/9$1,563

Sat 8/1111:20SYD - ORD

1 stop20h 21mAir Canada

Sat 15/1115:40ORD - SYD

1 stop24h 55mAir Canada

Deal found 23/9$1,588

Mon 13/1011:50SYD - ORD

2 stops29h 04mAir New Zealand

Thu 20/1112:45ORD - SYD

2 stops28h 45mAir New Zealand

Deal found 25/9$1,606

Wed 8/1011:50SYD - ORD

2 stops25h 34mAir New Zealand

Tue 21/1016:40ORD - SYD

2 stops24h 05mAir New Zealand

Deal found 23/9$1,613

Sun 9/1111:20SYD - MDW

2 stops41h 10mMultiple Airlines

Sun 16/1109:00MDW - SYD

2 stops31h 00mMultiple Airlines

Deal found 25/9$1,623

Wed 3/1212:25SYD - ORD

1 stop35h 55mANA

Mon 8/1218:05ORD - SYD

2 stops33h 10mANA

Deal found 24/9$1,706

Fri 10/1018:45SYD - ORD

1 stop21h 14mMultiple Airlines

Thu 23/1007:25ORD - SYD

1 stop32h 05mMultiple Airlines

Deal found 25/9$1,715

Tue 30/909:25SYD - MDW

2 stops24h 10mDelta

Wed 12/1109:34MDW - SYD

2 stops29h 56mDelta

Deal found 24/9$2,533

Fri 31/1009:40SYD - MDW

2 stops24h 15mDelta

Sun 2/1110:40MDW - SYD

2 stops28h 50mDelta

Deal found 25/9$2,609

Best flights from Sydney to Chicago
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 26 September 2025.

Thu 6/1109:55SYD - ORD

2 stops31h 20mAir New Zealand

Mon 10/1113:00ORD - SYD

2 stops28h 30mAir New Zealand

Deal found 24/9$1,441

Sun 9/1111:20SYD - MDW

2 stops41h 10mMultiple Airlines

Sun 16/1109:00MDW - SYD

2 stops31h 00mMultiple Airlines

Deal found 25/9$1,623

Thu 9/1010:10SYD - ORD

2 stops23h 07mAmerican Airlines

Wed 22/1014:57ORD - SYD

2 stops25h 08mAmerican Airlines

Deal found 24/9$1,743

Sat 8/1112:10SYD - ORD

2 stops24h 20mUnited Airlines

Sat 15/1115:43ORD - SYD

1 stop22h 17mUnited Airlines

Deal found 24/9$1,767

Tue 28/1010:20SYD - ORD

1 stop22h 24mAir Canada

Thu 30/1015:40ORD - SYD

1 stop24h 55mAir Canada

Deal found 24/9$2,107

Fri 31/1021:15SYD - ORD

2 stops53h 50mTurkish Airlines

Sun 2/1120:20ORD - SYD

2 stops54h 00mTurkish Airlines

Deal found 25/9$2,221

Fri 31/1015:15SYD - ORD

1 stop38h 40mCathay Pacific

Sun 2/1114:35ORD - SYD

1 stop28h 25mCathay Pacific

Deal found 25/9$2,222

Sat 8/1110:40SYD - MDW

2 stops24h 03mDelta

Sat 15/1109:32MDW - SYD

2 stops29h 58mDelta

Deal found 23/9$2,533

Wed 3/1211:45SYD - ORD

2 stops25h 40mAir New Zealand

Mon 8/1214:35ORD - SYD

2 stops26h 55mAir New Zealand

Deal found 25/9$1,565

Thu 9/1018:45SYD - ORD

1 stop21h 14mMultiple Airlines

Wed 22/1007:15ORD - SYD

2 stops32h 15mMultiple Airlines

Deal found 24/9$1,761

Sun 14/1212:10SYD - ORD

1 stop34h 52mUnited Airlines

Fri 2/107:35ORD - SYD

1 stop30h 25mUnited Airlines

Deal found 25/9$1,769

Wed 24/1212:10SYD - ORD

1 stop19h 45mUnited Airlines

Sat 24/119:58ORD - SYD

1 stop41h 22mUnited Airlines

Deal found 25/9$2,081

Thu 6/1110:40SYD - MDW

2 stops24h 03mDelta

Mon 10/1110:47MDW - SYD

2 stops28h 43mDelta

Deal found 24/9$2,533

Thu 25/1211:50SYD - ORD

1 stop25h 05mUnited Airlines

Fri 23/116:16ORD - SYD

1 stop21h 04mUnited Airlines

Deal found 25/9$2,154

Sun 26/1017:45SYD - MDW

2 stops45h 35mMultiple Airlines

Sun 2/1111:21MDW - SYD

1 stop26h 34mMultiple Airlines

Deal found 25/9$2,525

Fri 31/1009:40SYD - MDW

2 stops24h 15mDelta

Sun 2/1110:40MDW - SYD

2 stops28h 50mDelta

Deal found 25/9$2,609

Sun 26/1010:25SYD - MDW

2 stops24h 00mDelta

Sun 2/1105:00MDW - SYD

2 stops33h 30mDelta

Deal found 25/9$2,671

Thu 6/1114:00SYD - MDW

2 stops23h 39mMultiple Airlines

Mon 10/1118:27MDW - SYD

1 stop43h 28mMultiple Airlines

Deal found 24/9$2,734

Fri 24/1010:25SYD - MDW

2 stops27h 49mDelta

Fri 31/1013:08MDW - SYD

2 stops26h 22mDelta

Deal found 26/9$2,747

Wed 17/1210:40SYD - MDW

2 stops24h 38mDelta

Fri 2/111:48MDW - SYD

2 stops27h 42mDelta

Deal found 25/9$3,589

Sun 14/1210:40SYD - MDW

2 stops24h 38mDelta

Fri 2/111:48MDW - SYD

2 stops27h 42mDelta

Deal found 26/9$4,232

Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated 26 September 2025 and is based on user searches.

Tue 30/909:10SYD - ORD

1 stop36h 02mAmerican Airlines

Wed 12/1115:00ORD - SYD

1 stop25h 00mAmerican Airlines

Deal found 23/9$1,740

Tue 30/909:30SYD - ORD

2 stops22h 35mUnited Airlines

Wed 12/1116:17ORD - SYD

1 stop23h 58mUnited Airlines

Deal found 23/9$1,767

Tue 30/909:25SYD - MDW

2 stops24h 10mDelta

Wed 12/1109:34MDW - SYD

2 stops29h 56mDelta

Deal found 24/9$2,533

Thu 2/1009:25SYD - MDW

2 stops27h 11mDelta

Thu 9/1010:35MDW - SYD

2 stops29h 00mDelta

Deal found 23/9$3,241

Tue 7/1010:10SYD - ORD

2 stops44h 58mMultiple Airlines

Mon 20/1006:00ORD - SYD

2 stops34h 05mMultiple Airlines

Deal found 22/9$1,674

Tue 7/1010:10SYD - ORD

1 stop22h 40mAmerican Airlines

Mon 20/1019:01ORD - SYD

1 stop21h 04mAmerican Airlines

Deal found 22/9$1,755

Wed 8/1011:50SYD - ORD

2 stops25h 34mAir New Zealand

Tue 21/1016:40ORD - SYD

2 stops24h 05mAir New Zealand

Deal found 23/9$1,613

Thu 9/1010:10SYD - ORD

1 stop22h 40mAmerican Airlines

Wed 22/1015:14ORD - SYD

1 stop24h 51mAmerican Airlines

Deal found 24/9$1,757

Thu 9/1018:45SYD - ORD

1 stop21h 14mMultiple Airlines

Wed 22/1007:15ORD - SYD

2 stops32h 15mMultiple Airlines

Deal found 24/9$1,761

Sat 11/1010:30SYD - ORD

2 stops22h 35mUnited Airlines

Mon 27/1015:43ORD - SYD

1 stop23h 17mUnited Airlines

Deal found 23/9$1,659

Sat 11/1010:10SYD - ORD

2 stops23h 00mAmerican Airlines

Mon 27/1016:57ORD - SYD

2 stops24h 03mAmerican Airlines

Deal found 23/9$1,744

Fri 31/1009:40SYD - MDW

2 stops24h 15mDelta

Sun 2/1110:40MDW - SYD

2 stops28h 50mDelta

Deal found 25/9$2,609

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 26 September 2025.

Wed 15/1017:20SYD - ORD

2 stops27h 41mMultiple Airlines

Deal found 23/9$685

Wed 15/1017:20SYD - MDW

3 stops55h 11mMultiple Airlines

Deal found 25/9$831

Fri 10/1010:20SYD - ORD

2 stops29h 57mMultiple Airlines

Deal found 25/9$893

Sat 15/1117:45SYD - ORD

1 stop22h 15mMultiple Airlines

Deal found 25/9$947

Sun 26/1016:35SYD - ORD

1 stop32h 00mEtihad Airways

Deal found 23/9$964

Sun 26/1021:15SYD - ORD

3 stops42h 44mMultiple Airlines

Deal found 23/9$970

Thu 2/1017:45SYD - ORD

1 stop33h 14mMultiple Airlines

Deal found 23/9$971

Sat 15/1113:55SYD - ORD

2 stops22h 35mAir New Zealand

Deal found 25/9$992

Sat 15/1117:45SYD - MDW

2 stops34h 45mMultiple Airlines

Deal found 25/9$995

Fri 10/1018:45SYD - MDW

2 stops56h 54mMultiple Airlines

Deal found 25/9$1,017

Tue 30/921:30SYD - MDW

3 stops57h 28mMultiple Airlines

Deal found 24/9$1,539

Tue 30/909:25SYD - MDW

2 stops27h 11mDelta

Deal found 24/9$1,621

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 6/11

09:55-00:15

2 stops31h 20m

Chicago O'Hare Intl

Mon 10/11

13:00-10:30

2 stops28h 30m

$1,441

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 3/12

11:45-20:25

2 stops25h 40m

Chicago O'Hare Intl

Mon 8/12

14:35-10:30

2 stops26h 55m

$1,565

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 9/11

11:20-11:30

2 stops41h 10m

Chicago Midway

Sun 16/11

09:00-09:00

2 stops31h 00m

$1,623

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 9/10

10:10-17:17

2 stops23h 07m

Chicago O'Hare Intl

Wed 22/10

14:57-08:05

2 stops25h 08m

$1,743

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 9/10

18:45-23:59

1 stop21h 14m

Chicago O'Hare Intl

Wed 22/10

07:15-07:30

2 stops32h 15m

$1,761

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 8/11

12:10-19:30

2 stops24h 20m

Chicago O'Hare Intl

Sat 15/11

15:43-07:00

1 stop22h 17m

$1,767

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 14/12

12:10-06:02

1 stop34h 52m

Chicago O'Hare Intl

Fri 2/1

07:35-07:00

1 stop30h 25m

$1,769

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 24/12

12:10-14:55

1 stop19h 45m

Chicago O'Hare Intl

Sat 24/1

19:58-06:20

1 stop41h 22m

$2,081

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 28/10

10:20-16:44

1 stop22h 24m

Chicago O'Hare Intl

Thu 30/10

15:40-08:35

1 stop24h 55m

$2,107

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 25/12

11:50-19:55

1 stop25h 05m

Chicago O'Hare Intl

Fri 23/1

16:16-06:20

1 stop21h 04m

$2,154

Flights are sorted by cheapest return flights first.

Deals found on 23/9

Showing 1-10 of 39 results

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 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 Sydney to Chicago

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

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Sydney to Chicago by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Sydney to Chicago?

Travellers seeking maximum savings on their Sydney to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday at midday flights should be avoided if possible as fares are typically the most expensive at this time.

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

Los Angeles (LAX) – chosen by Cheapflights users on 72% of one-stop itineraries from Sydney to Chicago on Cheapflights.

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

Los Angeles (LAX) is the most affordable one-stop option, with an average return flight price of $1,595.

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

Flights via San Francisco (SFO) have the shortest average one-way travel time for one-stop routes: 19h 35m.

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

Flights via San Francisco (SFO) offer the fastest connection on this route, with an average stopover time of 1h 35m.

Reviews of airlines servicing Chicago

See what other customers who have flown with ANA, Air New Zealand, andQantas Airways from Sydney to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me

ANA

8.4

Very Good

972 reviews

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Air New Zealand

8.0

Very Good

506 reviews

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Qantas Airways

7.5

Good

908 reviews

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

United Airlines

7.4

Good

8,926 reviews

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Air Canada

7.1

Good

10,000 reviews

ANA

8.4

Very Good

972 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Related info for your journey

What airport do you fly from for flights from Sydney to Chicago?
For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.
How long is the flight from Sydney to Chicago?
Airlines like Air New Zealand, American Airlines, and United Airlines fly from Sydney to Chicago in about 23h 07m. The time it takes to get you to your destination can typically vary by up to 8h 13m. The distance between Sydney and Chicago is about 14851 km. Both multi-stop and direct flights can be found to your destination and back.
What are the cheapest airlines flying from Sydney to Chicago round-trip?
Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,002. Other airlines that can offer you cheap pricing are American Airlines, from $1,187, and Air Canada, from $1,201. You may be able to fly from Sydney to Chicago for 35% less than the average price by searching for these airlines.
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 holiday 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Fly from Sydney to Chicago on these airlines

Qantas Airways flights from Sydney Kingsford Smith to Chicago

Air Canada flights from Sydney Kingsford Smith to Chicago

ANA flights from Sydney Kingsford Smith to Chicago

Top 6 airlines flying from Sydney to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Qantas Airways	Cheapest$1,002	Average$1,146	FlexibilityNo cancel fee	On-time74%	Search Qantas Airways flights
American Airlines	Cheapest$1,187	Average$1,237	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
Air Canada	Cheapest$1,201	Average$1,683	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Air New Zealand	Cheapest$1,551	Average$1,610	FlexibilityNo cancel fee	On-time78%	Search Air New Zealand flights
ANA	Cheapest$1,599	Average$1,730	FlexibilityNo cancel fee	On-time80%	Search ANA flights
United Airlines	Cheapest$1,651	Average$2,439	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

Fly with Cheapflights

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

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Sydney to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Sydney.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Sydney to Chicago flexibly with Cheapflights today.

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

Of course! You can now track prices for flights from Sydney to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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Cheap flights from Sydney to Chicago from $685

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 15/10. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 82 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Sydney to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 26 September 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 26 September 2025.

Cheapflights Fare Finder

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

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 return flight from Sydney to Chicago. Price data was last updated on 19 September 2025.

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

Find hourly flight availability from Sydney to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 26 September 2025.

What is the cheapest day to fly from Sydney to Chicago?

Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 13 October 2024.

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

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

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

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

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

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

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

Average stopover duration for one-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

See what other customers who have flown with ANA, Air New Zealand, andQantas Airways from Sydney to Chicago have to say. You can also see how each airline compares in terms of 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 are the cheapest airlines flying from Sydney to Chicago round-trip?

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Sydney to Chicago on these airlines

Choose from the following airlines for your flight from Sydney to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 26 September 2025.

Top 6 airlines flying from Sydney to Chicago

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.

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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 26 September 2025.