CHI - SYD

$764 Find Cheap Flights from Chicago to Sydney

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Sydney departing on 4/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Sydney

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Sydney (CHI-SYD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Sydney that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Sydney

Mon, 27 Oct - Sun, 9 Nov
Multiple Airlines Logo
12:03 - 09:00MDW-SYD
28h 57m2 stops
Multiple Airlines Logo
14:05 - 22:03SYD-MDW
24h 58m2 stops
$1,548Multiple Airlines
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Mon, 20 Oct - Sun, 2 Nov
Multiple Airlines Logo
09:44 - 08:05MDW-SYD
30h 21m2 stops
Multiple Airlines Logo
14:05 - 23:03SYD-MDW
24h 58m2 stops
$1,607Multiple Airlines
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Sat, 28 Feb - Sat, 7 Mar
Fiji Airways Logo
16:45 - 12:30ORD-SYD
26h 45m2 stops
Fiji Airways Logo
14:10 - 19:18SYD-ORD
22h 08m2 stops
$1,652Fiji Airways
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Mon, 16 Feb - Sun, 1 Mar
ANA Logo
16:25 - 20:15ORD-SYD
34h 50m1 stop
ANA Logo
12:25 - 08:54SYD-ORD
37h 29m2 stops
$1,692ANA
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Tue, 17 Feb - Tue, 3 Mar
Hawaiian Airlines Logo
14:00 - 19:45ORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
21:40 - 13:04SYD-ORD
32h 24m2 stops
$1,701Hawaiian Airlines
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Tue, 24 Feb - Tue, 10 Mar
Hawaiian Airlines Logo
14:00 - 19:45ORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
21:40 - 13:04SYD-ORD
31h 24m2 stops
$1,703Hawaiian Airlines
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Tue, 3 Mar - Wed, 18 Mar
ANA Logo
16:25 - 20:15ORD-SYD
34h 50m1 stop
ANA Logo
12:25 - 09:37SYD-ORD
37h 12m2 stops
$1,715ANA
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Sat, 7 Feb - Sat, 14 Feb
Fiji Airways Logo
16:45 - 12:30ORD-SYD
26h 45m2 stops
Fiji Airways Logo
14:10 - 19:18SYD-ORD
22h 08m2 stops
$1,749Fiji Airways
Find Deal
Mon, 10 Nov - Wed, 26 Nov
Delta Logo
13:47 - 08:30MDW-SYD
25h 43m2 stops
Delta Logo
10:40 - 18:08SYD-MDW
24h 28m2 stops
$2,199Delta
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Mon, 9 Feb - Sun, 22 Feb
Delta Logo
10:35 - 08:30MDW-SYD
28h 55m2 stops
Delta Logo
10:40 - 18:08SYD-MDW
24h 28m2 stops
$2,200Delta
Find Deal

Everything you should know

Top airlines
Fiji Airways
Cheapest • from $1,652 (return)
Qantas Airways
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 12% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
$1,548
Multiple Airlines
Mon 27/10Sun 9/11
MDW - SYD • 2 stops
Cheapest one-way flight
$764
Typical prices: $622-821
Multiple Airlines
Wed 4/2
ORD - SYD • 2 stops
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Sydney!
Booking Insights

KAYAK's insights & trends for Chicago to Sydney flights

Get data-powered insights and trends into flights from Chicago to Sydney to help you find the cheapest flights, the best time to fly and much more.

How much is a return flight from Chicago to Sydney?

What’s the cheapest day of the week to fly from Chicago to Sydney?

The average price of all round-trip flights from Chicago to Sydney clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Sydney, you should consider leaving on a Friday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Sydney, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Sydney is August, where tickets cost $1,276 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $2,057 and $1,647 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Sydney, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Sydney, you should book around 3 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$764
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to Sydney

When to book flights from Chicago to Sydney

Are your dates flexible? Find out the best times to travel from Chicago to Sydney based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Sydney

  • Can I fly directly from Chicago to Sydney?

    Unfortunately, there aren’t any airlines with a direct connection from Chicago to Sydney. Your trips will involve at least one layover, with certain airlines even having two layovers scheduled for this trip. The location of the layover will depend on the airline you’re flying with. For instance, Air New Zealand has its layovers scheduled for Auckland while Air India has Delhi. Both American Airlines and United have Los Angeles as the set layover destination for this route.

  • Is public transport available from Sydney Airport (SYD) to downtown Sydney?

    Yes, there is a train that connects the airport to the city center. It is the cheapest option available and also the quickest, taking the best part of fifteen minutes between the airport and downtown. However, it is not as convenient as a taxi especially when you have a lot of luggage as it will drop you off at the Circular Quay in the center of Sydney then you will have to walk to your hotel.

  • What are the benefits of upgrading to first class for this trip?

    For a long flight like this one, you are sure to get maximum value for your money when you upgrade to first class. The seats are much more comfortable, making the trip more bearable, and you can stretch out freely with the extra legroom. In addition, you will be served an amazing selection of meals and drinks to enjoy at various points during the flight. Lastly, you will be able to access the first-class lounges during your layover, where you can freshen up and get some rest while waiting for the second leg of the flight.

  • Do I need a visa to fly from Chicago to Sydney?

    Yes, a visa is one of the mandatory requirements for all US citizens going to Sydney or any other Australian city. As they don’t provide any visas on arrival, you have to apply beforehand by visiting the Embassy or Consulate in advance of your travel dates to ensure that they have been processed by the time you’re flying out. You can also apply for an ETA via an online process, which is much more convenient.

  • What is the cheapest flight from Chicago to Sydney?

    In the last 3 days, the lowest price for a flight from Chicago to Sydney was $510 for a one-way ticket and $1,033 for a return.

  • Which airports will I be using when flying from Chicago to Sydney?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Sydney Kingsford Smith is the only airport in Sydney. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Sydney?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Sydney?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Sydney, with oneworld being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Chicago to Sydney?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Sydney.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Sydney?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sydney from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Sydney?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Sydney with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Sydney?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Sydney from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Sydney

  • Air New Zealand is a great option to book when flying with the entire family. They have free Wi-Fi available plus seatback on-demand video and free meals, all of which should make it a better experience for the kids.
  • The Blue Line train from downtown Chicago to O’Hare International Airport (ORD) is a good commuter option when you want to avoid the rush hour traffic that is usually quite a menace.
  • United Airlines doesn’t allow passengers to bring carry-on bags to the economy class cabin. However, they do allow one checked bag for free, meaning if you have any bags, you will need to check them before the flight.
  • American Airlines offers travelers the chance to calculate and offset the emissions generated during the flight from Chicago to Sydney through Cool Effect. This is a great way to make your trips more sustainable and keep the carbon footprint low.
  • Chicago Midway is an alternative departure airport to O’Hare. It is closer to downtown Chicago and also less busy, however, there are few flight options from the airport with all of them being served by Delta and including at least two layovers.

Reviews of the top airline flying from Chicago to Sydney

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sydney. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Sydney? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Qantas AirwaysOverall score based on 907 reviews
7.2Entertainment
7.7Boarding
7.5Comfort
8.2Crew
7.0Food
Airline reviews

A few more inches of legroom is all i ask

8.0 ExcellentTerry, Aug 2025CNS - SYD
Read more Qantas Airways reviews

A few more inches of legroom is all i ask

One of the best Qantas business flights I've had. Quality product

Business class points redemption - good value for points paid, dubious value if out of your own pocket, domestic class business product okay for this length of flight. The flight left and arrived on time, crew were good, aircraft was a bit old and tired, but still miles ahead of their competitors in Virgin and Jetstar.

Airline running better than post Covid, proper boarding process now implemented, some aircraft feeling a bit old and tired, crew fine, online experience better.

Five hour flight instead of four hours due to westerly headwinds which wasn’t the fault of Qantas !

The wifi was out. Otherwise it was great flight. Richard, as CSM, was excellent.

Was bumped to a later flight because of inefficiency on part of the airline.

The Emerits/Qantas flight was cancelled to Wellington. We need a refund. Had to buy another airline ticket. How do we get the refund. Still not in Wellington.

Delayed QF59 flight once again, Qantas doesn't fail in maintaining there delayed departures and arrivals. USB points do not work nor do the power point sockets on the plane, Qantas staff admitted that on the flight. Don't expect to your charge devices. Saving grace, was the ice cream. Bottom line, if you expect to fly to HND and make it on time avoid Qantas and if you're interested in ice cream - visit 7/11.

Pretty excellent. I don’t know what the pilot could have done better with the bumping ( there was a storm) nor what happened to my ears coming down into bendigo. It doesn’t happen coming down into Sydney just the return flight. I wonder why?

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

Information on your arrival and departure airports

Sydney (SYD)

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