How long is the flight from Sydney to Chicago?

Airlines like Air Canada, ANA, and United Airlines fly from Sydney to Chicago in about 19h 50m. The time it takes to get you to your destination can typically vary by up to 20h 56m. 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 $975. Other airlines that can offer you cheap pricing are American Airlines, from $1,160, and Air Canada, from $1,163. You may be able to fly from Sydney to Chicago for 32% 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 Qantas Airways, Air Canada or United Airlines as they are the most popular for this route.

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.

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. 7 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.

$926+ Flights from Sydney to Chicago

Q: How much does it cost for a return flight from Sydney to Chicago?

Airfare is typical for this route at the moment. Sydney to Chicago flights typically cost between $1,119 and $2,796 in April. The cheapest return flight price found within the last 3 days was $1,498 on Air New Zealand (20 Apr-6 May).

Cheap flight deals from Sydney to Chicago

Enter your travel dates to find the best prices.

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 28 December 2025.

Mon 29/1211:20SYD - ORD

1 stop36h 39mQantas Airways

Wed 31/1205:15ORD - SYD

1 stop32h 40mQantas Airways

Deal found 25/12$2,326

Mon 29/1212:10SYD - ORD

2 stops23h 35mUnited Airlines

Wed 31/1216:20ORD - SYD

1 stop21h 00mUnited Airlines

Deal found 25/12$2,516

Tue 30/1210:40SYD - MDW

2 stops22h 40mDelta

Thu 5/310:49MDW - SYD

2 stops27h 01mDelta

Deal found 28/12$2,595

Mon 29/1216:00SYD - ORD

2 stops43h 50mAir Canada

Wed 31/1220:30ORD - SYD

2 stops41h 25mAir Canada

Deal found 25/12$2,671

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 28 December 2025.

Wed 18/211:20SYD - ORD

2 stops40h 46mAir Canada

Sun 22/220:40ORD - SYD

2 stops43h 55mAir Canada

Deal found 27/12$1,655

Mon 1/620:55SYD - ORD

1 stop26h 45mANA

Mon 10/821:30ORD - SYD

2 stops30h 45mANA

Deal found 26/12$1,754

Thu 15/111:50SYD - ORD

1 stop19h 50mUnited Airlines

Fri 30/112:45ORD - SYD

1 stop24h 35mUnited Airlines

Deal found 26/12$1,801

Mon 9/211:20SYD - MDW

2 stops27h 59mMultiple Airlines

Mon 16/206:00MDW - SYD

2 stops34h 00mMultiple Airlines

Deal found 25/12$1,952

Sat 16/511:55SYD - ORD

2 stops24h 36mAir New Zealand

Sat 6/616:40ORD - SYD

2 stops25h 05mAir New Zealand

Deal found 26/12$1,985

Wed 3/609:15SYD - MDW

2 stops24h 16mDelta

Mon 10/814:00MDW - SYD

2 stops25h 35mDelta

Deal found 26/12$2,067

Fri 16/112:10SYD - ORD

2 stops21h 54mUnited Airlines

Fri 30/117:16ORD - SYD

1 stop22h 59mUnited Airlines

Deal found 25/12$1,875

Mon 1/609:20SYD - ORD

2 stops38h 40mAir Canada

Mon 10/805:15ORD - SYD

2 stops35h 05mAir Canada

Deal found 26/12$2,027

Tue 2/609:15SYD - MDW

2 stops27h 30mDelta

Mon 10/814:00MDW - SYD

2 stops25h 35mDelta

Deal found 26/12$2,067

Thu 28/509:20SYD - ORD

2 stops27h 39mAir Canada

Mon 10/805:15ORD - SYD

2 stops35h 05mAir Canada

Deal found 26/12$2,027

Thu 28/509:15SYD - MDW

2 stops27h 30mDelta

Mon 10/814:00MDW - SYD

2 stops25h 35mDelta

Deal found 26/12$2,067

Mon 1/609:15SYD - MDW

2 stops23h 50mDelta

Mon 10/814:00MDW - SYD

2 stops25h 35mDelta

Deal found 26/12$2,067

Sun 31/509:15SYD - MDW

2 stops23h 50mDelta

Mon 10/813:05MDW - SYD

2 stops26h 30mDelta

Deal found 26/12$2,141

Fri 12/609:15SYD - MDW

2 stops24h 16mDelta

Sun 12/714:00MDW - SYD

2 stops25h 35mDelta

Deal found 25/12$2,141

Tue 21/409:15SYD - MDW

2 stops23h 39mDelta

Thu 7/513:05MDW - SYD

2 stops26h 30mDelta

Deal found 27/12$2,143

Mon 9/210:40SYD - MDW

2 stops23h 49mDelta

Mon 16/213:49MDW - SYD

2 stops25h 41mDelta

Deal found 26/12$2,366

Mon 2/210:40SYD - MDW

2 stops23h 49mDelta

Wed 25/213:26MDW - SYD

2 stops26h 04mDelta

Deal found 27/12$2,367

Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated 28 December 2025 and is based on user searches.

Mon 29/1211:20SYD - ORD

1 stop36h 39mQantas Airways

Wed 31/1205:15ORD - SYD

1 stop32h 40mQantas Airways

Deal found 25/12$2,326

Thu 8/114:15SYD - MDW

2 stops24h 52mDelta

Thu 29/113:26MDW - SYD

2 stops24h 24mDelta

Deal found 27/12$2,857

Thu 15/112:10SYD - ORD

2 stops21h 54mUnited Airlines

Fri 30/112:53ORD - SYD

2 stops24h 27mUnited Airlines

Deal found 26/12$1,801

Fri 16/112:10SYD - ORD

2 stops21h 54mUnited Airlines

Fri 30/117:16ORD - SYD

1 stop22h 59mUnited Airlines

Deal found 25/12$1,875

Fri 16/114:00SYD - ORD

2 stops22h 51mUnited Airlines

Sat 31/116:16ORD - SYD

1 stop21h 04mUnited Airlines

Deal found 27/12$1,876

Fri 16/119:40SYD - ORD

2 stops36h 01mMultiple Airlines

Sat 31/111:15ORD - SYD

2 stops29h 20mMultiple Airlines

Deal found 27/12$1,969

Fri 16/119:15SYD - ORD

2 stops33h 40mQantas Airways

Fri 30/117:40ORD - SYD

2 stops44h 15mQantas Airways

Deal found 25/12$2,028

Fri 16/110:40SYD - MDW

2 stops28h 27mDelta

Fri 30/113:26MDW - SYD

2 stops26h 04mDelta

Deal found 25/12$2,164

Sat 24/111:20SYD - ORD

2 stops40h 46mAir Canada

Sat 31/121:15ORD - SYD

2 stops43h 20mAir Canada

Deal found 27/12$1,653

Sat 24/114:15SYD - MDW

2 stops25h 07mDelta

Sat 31/113:26MDW - SYD

2 stops24h 24mDelta

Deal found 27/12$2,518

Tue 27/111:20SYD - ORD

2 stops27h 45mAir Canada

Tue 24/215:35ORD - SYD

1 stop25h 00mAir Canada

Deal found 27/12$1,515

Tue 27/114:15SYD - MDW

2 stops25h 07mDelta

Tue 24/212:45MDW - SYD

2 stops25h 05mDelta

Deal found 27/12$2,367

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 28 December 2025.

Fri 16/112:35SYD - ORD

3 stops51h 09mMultiple Airlines

Deal found 26/12$926

Fri 6/212:35SYD - ORD

3 stops52h 15mMultiple Airlines

Deal found 27/12$960

Sun 22/221:50SYD - ORD

3 stops50h 45mMultiple Airlines

Deal found 27/12$1,013

Sat 31/112:35SYD - ORD

3 stops45h 35mMultiple Airlines

Deal found 25/12$1,036

Sat 31/111:45SYD - ORD

2 stops25h 40mAir New Zealand

Deal found 25/12$1,055

Thu 15/114:35SYD - ORD

3 stops40h 54mMultiple Airlines

Deal found 26/12$1,115

Wed 14/117:00SYD - ORD

3 stops38h 38mMultiple Airlines

Deal found 26/12$1,170

Tue 13/121:30SYD - ORD

3 stops58h 08mMultiple Airlines

Deal found 26/12$1,198

Mon 12/106:20SYD - ORD

3 stops58h 30mMultiple Airlines

Deal found 26/12$1,220

Tue 10/211:20SYD - ORD

2 stops25h 50mAir Canada

Deal found 27/12$1,222

Tue 13/114:15SYD - MDW

2 stops24h 52mDelta

Deal found 26/12$1,610

Sat 10/110:40SYD - MDW

2 stops22h 49mDelta

Deal found 26/12$1,957

Find flight deals from Sydney to Chicago

Round-trip from	$1,498
One-way from	$926
Popular in	December
Cheapest in	March
Average price	$2,040

Air New Zealand
20/4-6/5
4 total stops
50h 21m total
Sydney to Chicago

Search Deals

16/1
3 total stops
51h 09m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 19% potential increase in price ($519 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($82 potential savings vs. average return 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

Wed 18/2

11:20-11:06

2 stops40h 46m

Chicago O'Hare Intl

Sun 22/2

20:40-09:35

2 stops43h 55m

$1,655

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 1/6

20:55-08:40

1 stop26h 45m

Chicago O'Hare Intl

Mon 10/8

21:30-19:15

2 stops30h 45m

$1,754

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 15/1

11:50-14:40

1 stop19h 50m

Chicago O'Hare Intl

Fri 30/1

12:45-06:20

1 stop24h 35m

$1,801

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 16/1

12:10-17:04

2 stops21h 54m

Chicago O'Hare Intl

Fri 30/1

17:16-09:15

1 stop22h 59m

$1,875

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 9/2

11:20-22:19

2 stops27h 59m

Chicago Midway

Mon 16/2

06:00-09:00

2 stops34h 00m

$1,952

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 16/5

11:55-21:31

2 stops24h 36m

Chicago O'Hare Intl

Sat 6/6

16:40-08:45

2 stops25h 05m

$1,985

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 1/6

09:20-09:00

2 stops38h 40m

Chicago O'Hare Intl

Mon 10/8

05:15-07:20

2 stops35h 05m

$2,027

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 28/5

09:20-21:59

2 stops27h 39m

Chicago O'Hare Intl

Mon 10/8

05:15-07:20

2 stops35h 05m

$2,027

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 3/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Mon 10/8

14:00-06:35

2 stops25h 35m

$2,067

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/6

09:15-21:45

2 stops27h 30m

Chicago Midway

Mon 10/8

14:00-06:35

2 stops25h 35m

$2,067

Flights are sorted by cheapest return flights first.

Deals found on 26/12

Showing 1-10 of 33 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 52 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 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 $923). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,527). 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 for a return flight from Sydney to Chicago?

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

Los Angeles (LAX) – chosen by Cheapflights users on 73% 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 $1,519.

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

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

ANA

8.4

Very Good

1,049 reviews

ANA

8.4

Very Good

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

Air New Zealand

8.0

Very Good

562 reviews

ANA

8.4

Very Good

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

Qantas Airways

7.5

Good

957 reviews

ANA

8.4

Very Good

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

United Airlines

7.4

Good

9,114 reviews

ANA

8.4

Very Good

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

Air Canada

7.1

Good

10,562 reviews

ANA

8.4

Very Good

1,049 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Dec 2025

HND - LAX

I always take ANA because of the great service and overall experience.

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. 7 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 Canada, ANA, and United Airlines fly from Sydney to Chicago in about 19h 50m. The time it takes to get you to your destination can typically vary by up to 20h 56m. 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 $975. Other airlines that can offer you cheap pricing are American Airlines, from $1,160, and Air Canada, from $1,163. You may be able to fly from Sydney to Chicago for 32% 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.
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 $923). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,527). 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

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 7 airlines flying from Sydney to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Qantas Airways	Cheapest$976	Average$1,110	FlexibilityNo cancel fee	On-time74%	Search Qantas Airways flights
American Airlines	Cheapest$1,160	Average$1,209	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
Air Canada	Cheapest$1,163	Average$1,617	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Air New Zealand	Cheapest$1,408	Average$1,572	FlexibilityNo cancel fee	On-time78%	Search Air New Zealand flights
United Airlines	Cheapest$1,471	Average$2,264	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
ANA	Cheapest$1,563	Average$1,691	FlexibilityNo cancel fee	On-time80%	Search ANA flights
Virgin Australia	Cheapest$1,715	Average$2,780	FlexibilityNo cancel fee	On-time80%	Search Virgin Australia 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 $926

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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.

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 28 December 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 28 December 2025.

Find flight deals from Sydney to Chicago

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.

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 26 December 2025.

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

How much does it cost for a return flight from Sydney to Chicago?

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?

What is the cheapest month to book a flight 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 28 December 2025.

Top 7 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.

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

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

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

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

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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 28 December 2025.