SYD - CHI

$937 Find Cheap Flights from Sydney to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 8/12. 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 Chicago

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

Cheapest return fare
$1,537
Overall average: $1,733
Air New Zealand
Tue 18/11Tue 25/11
SYD - ORD • 2 stops
Cheapest one-way flight
$937
Typical prices: $1,733-$2,011
Air New Zealand
Mon 8/12
SYD - ORD • 2 stops
Top airlines
Air New Zealand
Cheapest • from $1,537 (return)
ANA
Best reviews • 8.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 27% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Sydney to Chicago (SYD-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Sydney to Chicago 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 Sydney to Chicago

Tue, 18 Nov - Tue, 25 Nov
Air New Zealand Logo
09:55 - 19:30SYD-ORD
26h 35m2 stops
Air New Zealand Logo
14:30 - 08:45ORD-SYD
25h 15m2 stops
$1,537Air New Zealand
Find Deal
Thu, 19 Feb - Thu, 26 Feb
Air New Zealand Logo
13:55 - 20:23SYD-ORD
23h 28m2 stops
Air New Zealand Logo
16:00 - 08:45ORD-SYD
23h 45m2 stops
$1,654Air New Zealand
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Multiple Airlines Logo
14:00 - 00:13SYD-ORD
27h 13m2 stops
Multiple Airlines Logo
06:50 - 12:35ORD-SYD
36h 45m2 stops
$1,722Multiple Airlines
Find Deal
Mon, 2 Feb - Thu, 19 Feb
Air Canada Logo
11:20 - 16:42SYD-ORD
22h 22m1 stop
Air Canada Logo
10:35 - 09:35ORD-SYD
30h 00m2 stops
$1,865Air Canada
Find Deal
Thu, 19 Feb - Thu, 26 Feb
Air Canada Logo
11:20 - 20:10SYD-ORD
25h 50m2 stops
Air Canada Logo
07:15 - 09:35ORD-SYD
33h 20m3 stops
$1,874Air Canada
Find Deal
Tue, 18 Nov - Tue, 25 Nov
ANA Logo
12:25 - 05:16SYD-ORD
33h 51m2 stops
ANA Logo
16:25 - 20:15ORD-SYD
34h 50m1 stop
$1,913ANA
Find Deal
Thu, 25 Dec - Sat, 24 Jan
United Airlines Logo
11:50 - 14:40SYD-ORD
19h 50m1 stop
United Airlines Logo
19:58 - 06:20ORD-SYD
41h 22m1 stop
$2,374United Airlines
Find Deal
Thu, 25 Dec - Fri, 23 Jan
American Airlines Logo
14:05 - 19:37SYD-ORD
22h 32m1 stop
American Airlines Logo
06:00 - 09:00ORD-SYD
34h 00m1 stop
$2,433American Airlines
Find Deal
Thu, 25 Dec - Fri, 23 Jan
United Airlines Logo
11:50 - 18:45SYD-ORD
23h 55m1 stop
United Airlines Logo
15:53 - 07:00ORD-SYD
22h 07m1 stop
$2,448United Airlines
Find Deal
Thu, 25 Dec - Thu, 22 Jan
American Airlines Logo
14:05 - 19:37SYD-ORD
22h 32m1 stop
American Airlines Logo
15:23 - 06:55ORD-SYD
22h 32m1 stop
$2,456American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Sydney to Chicago flights

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

How much is a return flight from Sydney to Chicago?

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

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

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

For Sydney to Chicago, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Sydney, the best deals are generally found on Friday, with Thursday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Sydney to Chicago, 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 Sydney to Chicago is March, where tickets cost $1,131 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $2,251 and $1,834 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Sydney to Chicago, 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 Sydney to Chicago, you should book around 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$937
Best time to beat the crowds (26% less expensive on average)
Most popular time to fly and prices are also 7% lower on average.
Flight from Sydney to Chicago O'Hare Airport

When to book flights from Sydney to Chicago

Are your dates flexible? Find out the best times to travel from Sydney to Chicago 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 Sydney to Chicago

  • What is the cheapest flight from Sydney to Chicago?

    In the last 3 days, the lowest price for a flight from Sydney to Chicago was $937 for a one-way ticket and $1,537 for a return.

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

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

  • Which airline alliances offer flights from Sydney to Chicago?

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

  • Which is the best airline for flights from Sydney to Chicago, ANA or Air New Zealand?

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are ANA and Air New Zealand. With an average price for the route of $1,868 and an overall rating of 8.4, ANA is the most popular choice. Air New Zealand is also a great choice for the route, with an average price of $1,638 and an overall rating of 8.0.

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

    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 Sydney to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Sydney 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 Sydney to Chicago?

    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 Chicago with an airline and back to Sydney with another airline.

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

    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 Chicago from Sydney up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines flying from Sydney to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Sydney to Chicago. 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 Sydney to Chicago? 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.
8.4
ANAOverall score based on 1003 reviews
7.9Entertainment
8.7Crew
7.7Food
8.6Boarding
8.2Comfort
Airline reviews

we were in premium economy, but we both got middle seats and had to sit separately. i could have avoided this by trying to obtain seats sooner, but i tried 3 times and gave up. ANA's technology is not friendly for newcomers. no, check that---I think it is nigh impossible. not sure we are coming back. ana can do better to provide a front end that's friendly to users in both US and Japan.

6.0 GoodAnonymous, Oct 2025HND - IAD
Read more ANA reviews

we were in premium economy, but we both got middle seats and had to sit separately. i could have avoided this by trying to obtain seats sooner, but i tried 3 times and gave up. ANA's technology is not friendly for newcomers. no, check that---I think it is nigh impossible. not sure we are coming back. ana can do better to provide a front end that's friendly to users in both US and Japan.

Checking in via an alliance partner, even a foreign one should get TSA Precheck printed on your boarding pass. The paper copy issued by ANA didn’t show it. I couldn’t get my digital copy due to some technical issue arising because I checked in with ANA. The kiosks at SFO similarly threw an error. The only way I could have gotten a new copy of my boarding pass was from the UA counter and lines were nearly as long as TSA so I bit the bullet and went through the regular TSA line. If UA wants my business, they need to improve that process.

Flight was diverted to Osaka due to engine problems then arrived at a different airport 6 hours late. We were so tired. ANA did the best they could.

Great as can be expected with a 10 hour flight over the Pacific. Great movie selection of new releases that hadn’t hit streaming yet. And despite the bad rep, I actually like the airplane good.

One of the best business class seats I’ve had. The lie flat seats made it comfortable to endure a 12 hour flight. Service was excellent and food was great.

Almost 6 hours of delay with over 12 gate changes. Flight was supposed to depart around 6 and instead depart after 12am. No accommodations were offered than some snacks closer to midnight when the crew was planning to throw away some snacks.

Purchased WiFi was slow to non functional. Staff was not personable or friendly. Seats were cramped. Boarding took long but I expected that.

The crew was excellent. The flight was delayed for 20 to 25 minutes. We did arrive a bit later than expected. The AC could have been better.

Very disappointed with the seat selection. During the booking, I selected seats such that my wife and I would sit next to each other. However, during check-in, we found out that the airline changed our seats and we were seated apart; and I was stuck in the middle seat with two strangers. Very disappointing experience. We would not fly ANA next time.

Luckily I just tried to sleep. But the entertainment system was awkward to operate. I hate all this stuff with apps and adding it to your phone and all. It is a nuisance. I would prefer a good magazine or newspaper in the pocket in front of me or available.

Kayak did not propagate my United miles account and I had to manually get credit.

Like: Aircraft was better than others I've flown in. Crew was great, food was very good. Air New Zealand is now my favorite airline. On our long flight from AKL to YVR there was enough room for those of us in Economy to stretch a bit. My sister is disabled and they took very good care of her and me. Best entertainment offering of all the other airlines. Not so much; Flight from AKL to YRV was delayed BUT they recovered really well so no complaints here. Pretty petty point to complain about. Only negative I have. I will recommend to friends.

Nice friendly staff and crew. Love the 787 flight. Get meals and lots of drinks!

Great entertainment options on the screen. uSB A and C chargers. Free WiFi! Crew were excellent.

Service was excellent and they’re very helpful and nice

Check in crew member was very helpful, nice and excellent service👍

Overall the plane was good and the crew great. The big disappointment was the skycouch. Maybe it would be good if you were a parent with 2 small kids travelling but as a couple it's hopeless. It's impossible for 2 adults to lie down so one ends up sitting. We split our time with one lying and the other sitting. We both got more sleep sitting upright. We will never book one again and don't recommend it to anyone.

Aircon set too high so VERY warm and VERY uncomfortable.

Not a comfortable trip, the seats are not good, and they look old.

Lost my luggage and brought someone else luggage to my airport.

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

No internet on flight, which makes log travels really hard.

My flight from Dallas to Sydney was cancelled. My entire trip was rerouted to include the following: Hartford to Washington DC Washington DC to JFK JFK to Auckland Auckland to Christchurch I paid for an aisle seat on the flight to Auckland and was asked if I would take a window seat to accommodate a family. The agent at the podium failed to mention that the family had a 3 month old baby and that a bassinet would be used during the 16 hour flight. The only way I could get out of my seat was to crawl under the bassinet of the sleeping baby. I think it is wrong that I was no given the choice to sit in another seat, that the agent knew what she was doing and chose to not properly disclose my seating arrangement. Terrible treatment.

they ran out of fruit for breakfast and so I just had a yogurt instead. other than that the flight was good

by the time they got to our row, they were out of some of the food options. games and movies were great but maybe more game options like tetris or pac man would be great

Great as usual, some delays but well communicated and made up for in the air

Poor! This flight was delayed 14 hours. There was no assistance in helping customers find other routes to their destination, nor any other kind of support. It was a chaotic experience. I'm not likely to fly with AA going forward.

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.

We were upgraded and after just a short delay in attending to a safety check we were on our way. Would definately fly Qantas International on their Dreamliner again.

I tried to check in online but was unable to do so. I stood in line for nearly two hours to check in. American Airlines was understaffed. When I finally got to the kiosk to check in, I was still unable to check in. No AA staff was available to help. Finally one of the airport security agents who was helping passengers became of lack of AA Staff told me: “I think the reason you can’t check in is that you are starting your name with an upper case letter when you write it. Just write it with all lower case letters.” That did allow me to check in. HOW COULD ANYONE POSSIBLY KNOW THAT IF THEY USE AN INITIAL UPPER CASE LETTER TO SPELL THEIR OWN NAME, AA WOULD NOT ALLOW THEM TO CHECK IN?????? Then I had to wait in line over half an hour again to drop off my baggage. Although I arrived at the airport 3 hours early, by the time I got to the gate, they had already started boarding.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

Air Canada cancelled our flight and reschedule it 26 hours later that completely interrupted my family's long waited Japan trip, it wasn't due to natural reason such as weather but under the company's control. On the day we wasted 9 hours of our time from 6am to 3pm, including a few hours in the customer counter waiting for supervisor to handle our rescheduling. When we came to the counter for rebooking help there were at least 4 employees on the counter but we were told they were not trained to handle customer rebooking, we were also told the supervisor could come 10:30 to handle our rebooking, but she showed up more than one hour later, the end result was exactly the same so the few hours we spent waiting for her was completely wasted; We already prepaid hotel and all the tickets for the our stay in Tokyo so all of the cost for the first day is completed wasted; The $80 meal voucher issues was far less than our financial loss due to the financial cancellation, and it was not surprisingly invalid (as Your company screw up everything possible along the flight), the vouchers were supposed to last 72 hours, when we tried to used it at our lounge next day less than 24 hours from its issuing at a designated restaurant, the worker there couldn't scan the vouchers after multiple tries on all 4 vouchers issued, so we had to pay the food from our own money; For the two return flights they were also full of unfortunate events that caused bad experience and further delay and waste of our time, both flights departed late and the last leg had another significant delay of more than half an hour after touchdown, the gate was for some reason not available so we waited more than half an hour, when we got out of plane it was almost one hour later than the supposed arrival time; The gate you arranged is the farthest in Vancouver airport, also was the luggage pickup location in Seattle airport; We also called customer service for rescheduling help and after a long time wait (more than an hour) we got a call back but the CS representative was equally clueless and unhelpful. Other than a fatal crash, your company couldn't do anything right and provided the worst service possible among the tons of flights we have taken in our lives.

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

It was crazy, boarded over a hour late from scheduled departure. Then when arrived in BNA issued with getting off the plane…over 1/2 hour. Not looking forward to flying Air Canada, ever again.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

The flight attendants were not very nice. No smiles On my return trip I was charged for one bag $83.30 although I had purchased the flight including one piece of luggage. Can this be refunded to me? Thank you!

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

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

Other airlines flying from Sydney to Chicago

Flights from the other most popular airlines that fly from Sydney to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.