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 $1,330 and $1,845 in September. The cheapest return flight price found within the last 3 days was $1,538 on Multiple Airlines (4 Sept-19 Sept). Find deals

Question 1

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

Accepted Answer

Airfare is typical for this route at the moment.Sydney to Chicago flights typically cost between $1,330 and $1,845 in September.
The cheapest return flight price found within the last 3 days was $1,538 on Multiple Airlines (4 Sept-19 Sept). Find deals

Question 2

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

Accepted Answer

Flights via Houston (IAH) offer the fastest connection on this route, with an average stopover time of 1h 33m. Find deals

Question 3

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

Accepted Answer

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

Question 4

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

Accepted Answer

Flights via Houston (IAH) have the shortest average one-way travel time for one-stop routes: 19h 57m. Find deals

Question 5

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

Accepted Answer

Los Angeles (LAX) is the most affordable one-stop option, with an average return flight price of $1,684.

Question 6

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

Accepted Answer

Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,011. Other airlines that can offer you cheap pricing are American Airlines, from $1,196, and Air Canada, from $1,268. You may be able to fly from Sydney to Chicago for 36% less than the average price by searching for these airlines.

Question 7

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

Accepted Answer

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.

Question 8

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

Accepted Answer

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.

Question 9

E

Accepted Answer

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.

Question 10

E

Accepted Answer

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).

Question 11

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

Accepted Answer

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.

Question 12

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

Accepted Answer

Flying to your destination on a Friday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

Question 13

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

Accepted Answer

Travellers have found it’s best to book a flight 44 days in advance to save up to 49% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 44 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Sydney to Chicago 1-2 weeks in advance for as low as $1,710, or $2,426 for flights within the next 24 hours.

Question 14

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

Accepted Answer

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, February can be a great choice for travel to Chicago. Flights to Chicago from Sydney in February are about $1,590 on average during February, but can be found for as low as $981.

Question 15

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

Accepted Answer

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.

Question 16

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

Accepted Answer

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.

Question 17

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

Accepted Answer

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

Question 18

How can I find direct flights from Sydney to Chicago?

Accepted Answer

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

Question 19

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

Accepted Answer

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.

Question 20

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

Accepted Answer

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.

Question 21

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

Accepted Answer

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.

Question 22

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

Accepted Answer

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

Question 23

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

Accepted Answer

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.

Round-trip from	$1,538
One-way from	$589
Popular in	December
Cheapest in	February
Average price	$1,593

Airline	Cheapest	Average	Flexibility	On-time
Qantas Airways	Cheapest$1,011	Average$1,166	FlexibilityNo cancel fee	On-time74%	Search Qantas Airways flights
American Airlines	Cheapest$1,196	Average$1,247	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
Air Canada	Cheapest$1,268	Average$1,735	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Air New Zealand	Cheapest$1,563	Average$1,622	FlexibilityNo cancel fee	On-time78%	Search Air New Zealand flights
ANA	Cheapest$1,611	Average$1,803	FlexibilityNo cancel fee	On-time80%	Search ANA flights
United Airlines	Cheapest$1,664	Average$2,460	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Virgin Australia	Cheapest$1,767	Average$2,865	FlexibilityNo cancel fee	On-time80%	Search Virgin Australia flights

Cheap flights from Sydney to Chicago from $589

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 February or March, booked 82 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Sydney to Chicago

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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 15 August 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 15 August 2025.

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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 8 August 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 15 August 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.

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?

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?

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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 15 August 2025.

Top 7 airlines flying from Sydney to Chicago

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

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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 15 August 2025.