SYD - CHI

$876 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 4/11. 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 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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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

Sat, 8 Nov - Sun, 23 Nov
Air New Zealand Logo
13:55 - 19:30SYD-ORD
22h 35m2 stops
Air New Zealand Logo
14:30 - 08:45ORD-SYD
25h 15m2 stops
$1,482Air New Zealand
Find Deal
Thu, 4 Dec - Thu, 11 Dec
Air New Zealand Logo
11:45 - 19:44SYD-ORD
24h 59m2 stops
Air New Zealand Logo
14:35 - 10:30ORD-SYD
26h 55m2 stops
$1,548Air New Zealand
Find Deal
Mon, 3 Nov - Sat, 8 Nov
Air New Zealand Logo
13:55 - 19:30SYD-ORD
22h 35m2 stops
Air New Zealand Logo
13:00 - 08:45ORD-SYD
26h 45m2 stops
$1,591Air New Zealand
Find Deal
Mon, 10 Nov - Tue, 25 Nov
Air Canada Logo
11:20 - 14:41SYD-ORD
20h 21m1 stop
Air Canada Logo
15:40 - 09:35ORD-SYD
24h 55m1 stop
$1,634Air Canada
Find Deal
Mon, 10 Nov - Tue, 25 Nov
Air Canada Logo
11:20 - 14:41SYD-ORD
20h 21m1 stop
Air Canada Logo
07:05 - 09:35ORD-SYD
33h 30m2 stops
$1,661Air Canada
Find Deal
Sun, 9 Nov - Mon, 24 Nov
Qantas Airways Logo
11:20 - 17:45SYD-ORD
23h 25m1 stop
Qantas Airways Logo
18:23 - 09:00ORD-SYD
21h 37m1 stop
$1,806Qantas Airways
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Wed, 3 Dec - Wed, 10 Dec
Qantas Airways Logo
11:20 - 16:02SYD-ORD
21h 42m1 stop
Qantas Airways Logo
18:17 - 09:00ORD-SYD
21h 43m1 stop
$1,811Qantas Airways
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Mon, 17 Nov - Mon, 24 Nov
American Airlines Logo
11:20 - 17:58SYD-ORD
23h 38m2 stops
American Airlines Logo
15:13 - 09:00ORD-SYD
24h 47m2 stops
$1,815American Airlines
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Mon, 17 Nov - Mon, 24 Nov
American Airlines Logo
11:20 - 23:59SYD-ORD
29h 39m1 stop
American Airlines Logo
11:40 - 09:00ORD-SYD
28h 20m1 stop
$1,827American Airlines
Find Deal
Mon, 17 Nov - Mon, 24 Nov
ANA Logo
21:45 - 05:16SYD-ORD
48h 31m2 stops
ANA Logo
10:30 - 20:15ORD-SYD
40h 45m1 stop
$1,921ANA
Find Deal

Everything you should know

Top airlines
Air New Zealand
Cheapest • from $1,482 (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
Cheapest return fare
$1,482
Typical prices: $1,665-$1,838
Air New Zealand
Sat 8/11Sun 23/11
SYD - ORD • 2 stops
Cheapest one-way flight
$876
Typical prices: $1,460-$1,572
Air Canada
Tue 4/11
SYD - ORD • 1 stop
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We hope you love your trip to Chicago!
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 November.

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 $1,130 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $2,339 and $1,832 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$876
Best time to beat the crowds (27% 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 $876 for a one-way ticket and $1,482 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 $1,866 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 $1,634 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 990 reviews
7.9Entertainment
8.6Boarding
8.7Crew
7.7Food
8.2Comfort
Airline reviews

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.

10.0 ExcellentAnonymous, Sept 2025NRT - SFO
Read more ANA reviews

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.

Upgrade the comfort, food and attendants. Also we arrived in Houston in the morning. The meal they served two hours before our arrival was a dinner entree. It would have been a lot nicer and much more appropriate to have had breakfast.

Wonderful I would recommend it to fly & ride with ANA.

Poor. We weren’t able to check in online (for several hours until we gave up) for no apparent reasons although our passports were loaded successfully. When we were at the airport check-in, a rep helped us at the kiosk but she disregarded the KTN provided to her so we had to come back for it after being questioned by the TSA person…

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.

Not entirely positive. It’s frustrating that everything is done through the united app. One of our flight attendants on our trip from San Francisco to MSP continually had trouble hearing people so she flipped her hair into people’s faces

I flew United from San Francisco to Auckland. My connecting flight from Auckland to Christchurch was canceled with no explanation. I was finally told the cancellation was due to fog. Even though it was clear when we landed. I am from San Francisco, I know what fog is! And I didn't see any fog. I was told the next available flight was 7 hours later. Unacceptable, they should have had a flight ready to go as soon as it was deemed safe to take off.

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.

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!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

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 airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

taking our carryon and forcing us to check it through

Wifi was great. Kind air crew and comfortable seating. Also liked the entertainment options.

Great flight. Only complaint is it took over an hour for my luggage to get to the carousel on the return to LAX That was irritating

I knew I was going to fall asleep unsettlingly from exhaustion so I warned the guy next to me in advance. The attendant took to checking on me frequently and even insisted I take my snack because I said no while sleep hazed and then absolutely wanted it about 5 minutes later. He was So caring and kind to my situation!!

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

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.

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