CHI - SYD

$593 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 7/29. 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
$1,305
Typical prices: $1,433-$845
ANA
sáb. 11/7mié. 11/18
ORD - SYD • 2 stops
Cheapest one-way
$593
Typical prices: $972-$1,194
Multiple Airlines
mié. 7/29
ORD - SYD • 3 stops
Top airlines
Cheapest • from $1,305 (round-trip)
Best reviews • 8.3 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Sydney. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $238 (round-trip)
Shortest trip • 14h 05m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 14% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 65% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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

sáb., nov. 7 - mié., nov. 18
ANA Logo
8:00 pm - 8:15 pm
ORD
-
SYD
31h 15m
2 stops
ANA Logo
9:45 pm - 7:20 am
SYD
-
ORD
26h 35m
1 stop
$1,305ANA
mié., ago. 26 - mar., sep. 1
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
$1,307ANA
jue., ago. 13 - dom., ago. 23
ANA Logo
5:45 pm - 9:25 am
ORD
-
SYD
24h 40m
1 stop
ANA Logo
8:55 pm - 4:41 pm
SYD
-
ORD
34h 46m
2 stops
$1,309ANA
vie., nov. 6 - jue., nov. 19
ANA Logo
4:25 pm - 8:15 pm
ORD
-
SYD
34h 50m
1 stop
ANA Logo
12:25 pm - 3:15 pm
SYD
-
ORD
43h 50m
2 stops
$1,310ANA
dom., jun. 21 - mar., jul. 7
Air Canada Logo
8:45 am - 7:20 am
ORD
-
SYD
31h 35m
1 stop
Air Canada Logo
9:20 am - 2:36 pm
SYD
-
ORD
20h 16m
1 stop
$1,313Air Canada
mié., ago. 12 - dom., ago. 23
ANA Logo
7:50 pm - 9:25 am
ORD
-
SYD
46h 35m
2 stops
ANA Logo
8:55 pm - 4:41 pm
SYD
-
ORD
34h 46m
2 stops
$1,314ANA
dom., jun. 21 - mar., jul. 7
Air Canada Logo
8:45 am - 7:20 am
ORD
-
SYD
31h 35m
1 stop
Air Canada Logo
9:20 am - 2:36 pm
SYD
-
ORD
20h 16m
1 stop
$1,319Air Canada
lun., nov. 2 - vie., nov. 20
Delta Logo
1:00 pm - 8:30 am
MDW
-
SYD
26h 30m
2 stops
Delta Logo
10:40 am - 4:50 pm
SYD
-
MDW
23h 10m
2 stops
$1,464Delta
vie., ago. 14 - dom., ago. 30
Multiple Airlines Logo
11:06 am - 7:05 am
MDW
-
SYD
28h 59m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,534Multiple Airlines
mié., ago. 12 - dom., ago. 23
Delta Logo
1:51 pm - 6:50 am
MDW
-
SYD
25h 59m
2 stops
Delta Logo
9:15 am - 6:01 pm
SYD
-
MDW
23h 46m
2 stops
$1,613Delta
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 November.

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 October and June, where the average cost of round-trip tickets is $831 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 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$593
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 23% 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 5 days, the lowest price for a flight from Chicago to Sydney was $593 for a one-way ticket and $1,305 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 Air New Zealand?

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Air New Zealand. With an average price for the route of $1,256 and an overall rating of 8.3, ANA is the most popular choice. Air New Zealand is also a great choice for the route, with an average price of $1,522 and an overall rating of 8.0.

  • 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 1230 reviews
7.9Entertainment
8.2Comfort
7.7Food
8.5Boarding
8.7Crew
Airline reviews

As usual the flight from AUS in Austin to SFO was late because they didn’t have adequate staffing to board the plane on time creating a 1 hour delay, which resulted in me missing my flight to Osaka due to a missed connection. When I got to the gate 10 minutes late after landing exactly the time the connecting flight was taking off, I saw my flight to Osaka sitting at the gate and that gates had closed. I attempted to contact United Via chat on the United App and was given the runaround and passed between 2 separate “agents” who after saying they could rebook me, told me I needed to go to ANA even though they’re partners and all of my ticketing was through United. After going to ANA’s gate at SFO to try and get help I was told I would need to leave and go to United’s ticket counter in order to get help. The ANA agents said that it was United’s issue. An hour after running to try to make my flight I got to the United counter. I showed the agent my itinerary and she helped as much as she could. I was booked on a flight that would occur 13 hours after my original flight to Osaka and given $45 in vouchers which doesn’t cover much at SFO. I had also spent 30000 miles with United to get an upgrade with more legroom. And that was not refunded to this point. Ultimately I lost 1 whole day of vacation in with my wife and kids and, the 30000 airline miles and I’m out the money and time I spent. In these situations United and their partners should go out of their way to communicate and accommodate but I was left to my own devices to find the right resources. The only option was to fly to Seoul 12 hours and take a connecting flight to Osaka: I am a United Skyniles member and would not recommend booking a flight with them unless you thoroughly understand the routes as it is likely you will be left to your own devices to resolve the situation.

2.0 Mediocremizue, Jun 2026
AUS - SFO
Read more ANA reviews

As usual the flight from AUS in Austin to SFO was late because they didn’t have adequate staffing to board the plane on time creating a 1 hour delay, which resulted in me missing my flight to Osaka due to a missed connection. When I got to the gate 10 minutes late after landing exactly the time the connecting flight was taking off, I saw my flight to Osaka sitting at the gate and that gates had closed. I attempted to contact United Via chat on the United App and was given the runaround and passed between 2 separate “agents” who after saying they could rebook me, told me I needed to go to ANA even though they’re partners and all of my ticketing was through United. After going to ANA’s gate at SFO to try and get help I was told I would need to leave and go to United’s ticket counter in order to get help. The ANA agents said that it was United’s issue. An hour after running to try to make my flight I got to the United counter. I showed the agent my itinerary and she helped as much as she could. I was booked on a flight that would occur 13 hours after my original flight to Osaka and given $45 in vouchers which doesn’t cover much at SFO. I had also spent 30000 miles with United to get an upgrade with more legroom. And that was not refunded to this point. Ultimately I lost 1 whole day of vacation in with my wife and kids and, the 30000 airline miles and I’m out the money and time I spent. In these situations United and their partners should go out of their way to communicate and accommodate but I was left to my own devices to find the right resources. The only option was to fly to Seoul 12 hours and take a connecting flight to Osaka: I am a United Skyniles member and would not recommend booking a flight with them unless you thoroughly understand the routes as it is likely you will be left to your own devices to resolve the situation.

The food was terrible and totally inedible. If you are flying with ANA/United bring your own food it was a long flight to be hingry

Staff at gate and crew on plane efficient and friendly.

I thought I bought the ticket directly through Kayak not a 3rd party

I like that we made it faster than regularly scheduled. Everything else was poor. The boarding was slow and chaotic. One person was screaming instructions to people that didn’t understand and there was only one camera so boarding was slow. The crew was not very friendly and one stewardess was extremely rude to everyone the entire flight. The food was not good and not themed to the country we were going to like every international flight I’ve taken. Lastly the seats were awful. After this flight I would never recommend United and will actively avoid booking another flight through them.

When I checked in, it printed two bag tags. The helper said they would cancel the other. They canceled both and my bag was left behind

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

Boarding was effortless, the food was outstanding, the seats in Premium Economy were extremely comfortable, and the staff and crew were excellent.

I never flew with alliance. Kayak is a joke and none of the flights or times were correct. Won’t ever use kayak again

I missed my flight due to unforeseen circumstances It was, however , an excellent price !

We had a medical emergency, needing to get to an emergency room upon landing at LAX. I let the back flight attendants know the situation. One, David, contacted the pilot, who made arrangements for EMT's to be there when we got off the plane. They went above and beyond for us. We didn't have to go through customs, as a customs person came to us and checked us right at the exit of the jet way. Another wonderful woman, a United employee at LAX, perhaps a customer service liaison, took care of our luggage situation, as we weren't going to make our connection to Bozeman. When we came back to LAX to see when we could get a flight to Bozeman, the personnel are very accommodating and booked us on the next flight out, and assigned good seats. It was a horrible flight, physically, from Sydney to LAX, , but the professionalism of all involved was excellent! We are very grateful fir the way they all stepped in and helped during a very unpleasant medical situation. Thank you!!

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.

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.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

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.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

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.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

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.

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

Information on your arrival and departure airports