CHI - SYD

$534 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 8/24. 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, 0 bags

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney.
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Everything you should know

Cheapest round-trip
$1,178
Typical prices: $1,519-$1,329
Multiple Airlines
Mon 9/14Sun 9/20
ORD - SYD • 3 stops
Cheapest one-way
$534
Typical prices: $769-$920
Multiple Airlines
Mon 8/24
ORD - SYD • 2 stops
Top airlines
Cheapest • from $1,231 (round-trip)
Best reviews • 8.3 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Chicago and Sydney. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $782 (round-trip)
Shortest trip • 18h 53m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 10% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 68% price drop
Most popular
Good to know
Good to know
+1
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Flight Deals
Booking Insights
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 round-trip 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 round-trip flight deals from Chicago to Sydney

Mon, Sep 14 - Sun, Sep 20
Multiple Airlines Logo
11:49 am - 11:50 am
ORD
-
SYD
33h 01m
3 stops
Multiple Airlines Logo
1:15 pm - 10:48 am
SYD
-
ORD
36h 33m
3 stops
$1,178Multiple Airlines
Wed, Aug 26 - Tue, Sep 8
ANA Logo
5:45 pm - 9:25 am
ORD
-
SYD
24h 40m
1 stop
ANA Logo
8:55 pm - 8:40 am
SYD
-
ORD
26h 45m
1 stop
$1,231ANA
Tue, Aug 25 - Sun, Sep 6
ANA Logo
5:45 pm - 9:25 am
ORD
-
SYD
24h 40m
1 stop
ANA Logo
8:55 pm - 2:55 pm
SYD
-
ORD
33h 00m
1 stop
$1,232ANA
Tue, Aug 25 - Sun, Sep 6
ANA Logo
7:50 pm - 7:10 pm
ORD
-
SYD
32h 20m
2 stops
ANA Logo
8:55 pm - 2:55 pm
SYD
-
ORD
33h 00m
1 stop
$1,237ANA
Wed, Aug 5 - Sun, Aug 30
ANA Logo
5:45 pm - 7:10 pm
ORD
-
SYD
34h 25m
1 stop
ANA Logo
11:45 am - 4:45 am
SYD
-
ORD
32h 00m
2 stops
$1,240ANA
Wed, Aug 5 - Sun, Aug 30
ANA Logo
5:45 pm - 7:10 pm
ORD
-
SYD
34h 25m
1 stop
ANA Logo
11:45 am - 4:45 am
SYD
-
ORD
32h 00m
2 stops
$1,241ANA
Wed, May 27 - Sun, Jun 7
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,511Multiple Airlines
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:49 pm - 6:50 am
MDW
-
SYD
26h 01m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,756Delta
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:49 pm - 6:50 am
MDW
-
SYD
26h 01m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,757Delta
Wed, Aug 26 - Wed, Sep 2
Delta Logo
1:00 pm - 6:50 am
MDW
-
SYD
26h 50m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,831Delta
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 round-trip flight from Chicago to Sydney?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Sydney departing in September.

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 $138 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $845 and $793 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 5 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$534
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 8% increase in price.
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 round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips 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 $534 for a one-way ticket and $1,178 for a round-trip.

  • Do I need a passport to fly between Chicago and Sydney?

    Yes, you’ll need a passport to travel to Sydney from Chicago.

  • 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?

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

  • What is the most popular layover when flying to Sydney from Chicago?

    Los Angeles is the most popular layover city among KAYAK users traveling from Chicago to Sydney.

  • Which is the best airline for flights from Chicago to Sydney, ANA or Fiji Airways?

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Fiji Airways. With an average price for the route of $1,256 and an overall rating of 8.3, ANA is the most popular choice. Fiji Airways is also a great choice for the route, with an average price of $1,155 and an overall rating of 8.1.

  • 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 round-trip 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 5 airlines serving 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.
8.3
ANAOverall score based on 1202 reviews
8.2Comfort
8.7Crew
8.5Boarding
7.7Food
7.9Entertainment
Airline reviews

The ladies are great seats should be a little bigger!

10.0 ExcellentJINJI JOO, Apr 2026
LAX - NRT
Read more ANA reviews

The ladies are great seats should be a little bigger!

Couple of hours delayed, we had to re-booked our Shinkansen reservation twice. United Aiines need to improve their time!

The staff is amazing, I cannot stress that enough! The food is really good and snacks at stations to take for yourselves. Economy seating is fine, not the most comfortable, but our friends in Premium Economy said they were very comfortable! Decent entertainment options, but being built in, you have to use their cheap headsets unless you have your own plug in ones. I only have Bluetooth earbuds.

It was good. The crew was efficient, food was good

Seats were extremely cramped even for economy. Food was atrocious. Crew was fine but no follow up, additional drinks offered etc. For a 14 hour flight I expected more.

Boarding was good. Inflight service was good. Alcoholic drinks could have been served free.

Suite lounge in Honolulu is the best lounge in Honolulu. I love the huge bathrooms in ANA first Class on the A380 Honu plane. Japanese meal was outstanding and service was amazing. Everything was just excellent. Can’t wait to fly again

Their was $200 charge for 2nd luggage, airplane very new and flight smooth. Flight time seem faster then Asian stoping Korea then china.

Flight was late boarding. United crew were not friendly and cordial unlike the ANA crew.

Seat was broken. Check in was not possible until we reached the gate, by then we were separated.

PREMIUM ECONOMY - excellent !Brilliant new plane. Excellent tv catalogue. Good food. Good communication and service from all friend Australian crew. Good communication from captain. Best travel experience in years.

Very good overall. However, your choices of free movies was limited and there was no music Channel???

I couldn't hear all of the announcements. It was nice when they put them on the screen.

This was the worst flight I’ve been on. Getting on the plane where is was 30 degrees outside was hotter on board cabin must’ve been 33 degrees. This is a health hazard. They cannot be doing this to save on fuel. People could die from this!!. Fans and a/c was, off entertainment was off. Poor excuse given. Crew made the excuse that the system didn’t have enough power. They basically were operating on one engine to save on jet fuel till 3 hours later on cruising altitude and they then started the second engine. And finally the cabin was cooled. On a 7hour red eye flight this made it so uncomfortable and impossible to sleep.

My experience was great overall. Tanya was particularly friendly and helpful the entire trip. I was very pleased with her customer service skills. The plane was an older aircraft but the entire way was comfortable with barely any turbulence at all. Qantas should speed up its fleet renovation. Totally recommend using this airline.

Qantas is always subpar beyond comfy chairs for a domestic flight

I liked boarding the plane. The staff were rude, the food was appalling and the chairs the most uncomfortable I have ever experienced

an hour late, then had to disembark on back stairs and take 4 flights up to get to main airport. No warning, and difficulty for those with canes and poor knees.

Well my expórtenle with Qantas it wasn’t that good KLM from Bs Aires was delay Santiago Chile Qantas QF 028 was still in the airport but the crew didn’t opened the door for me soo I lost my fly And I stuck in the airport 13 hrs waiting for next fly by Latam Arline My question is can I have my money back for business class

It was ok, the additional baggage charges were a bit excessive given winter is a time for skiing. To have to pay $600 extra for skis was tantamount to robbery. Airlines should consider sporting goods as baggage. Likewise, they should consider increasing the number of bags allowed on international flights to known ski destinations.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

My original booking was through AirCanada and unbeknownst to me they altered flights and providers which caused a complete disaster for checking in for my flights and seat assignments. The original gate agent in Auckland had me basically doing gymnastics to get onto the future flights and have my luggage follow me.

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

I think overall both Air Canada and Air New Zealand did a good job the their flights. It is nice to have movies, music, podcasts etc to watch for the long flights. Just wish the seats were wider and had a foot rest to change my leg positions during the trips.

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

Information on your arrival and departure airports