SYD - CHI

$813 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 15/11. 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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Flights 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

Fri, 8 Aug - Sat, 23 Aug
 Logo
13:15 - 05:25SYD-ORD
31h 10m2 stops
 Logo
07:05 - 11:45ORD-SYD
37h 40m2 stops
$1,430
Find Deal
Wed, 27 Aug - Wed, 3 Sep
 Logo
13:15 - 05:40SYD-ORD
31h 25m2 stops
 Logo
07:05 - 11:45ORD-SYD
37h 40m2 stops
$1,511
Find Deal
Sun, 10 Aug - Sun, 17 Aug
 Logo
09:20 - 06:03SYD-ORD
35h 43m3 stops
 Logo
07:05 - 07:20ORD-SYD
33h 15m2 stops
$1,534
Find Deal
Sat, 26 Jul - Tue, 11 Nov
Air New Zealand Logo
11:50 - 22:59SYD-ORD
26h 09m2 stops
Air New Zealand Logo
14:30 - 08:45ORD-SYD
25h 15m2 stops
$1,619Air New Zealand
Find Deal
Sun, 24 Aug - Sun, 31 Aug
ANA Logo
11:50 - 05:01SYD-ORD
32h 11m2 stops
ANA Logo
17:45 - 09:25ORD-SYD
24h 40m1 stop
$1,698ANA
Find Deal
Sat, 2 Aug - Tue, 19 Aug
Air New Zealand Logo
09:55 - 04:51SYD-ORD
33h 56m2 stops
Air New Zealand Logo
16:30 - 08:45ORD-SYD
25h 15m2 stops
$1,708Air New Zealand
Find Deal
Wed, 5 Nov - Thu, 13 Nov
ANA Logo
12:25 - 05:16SYD-ORD
33h 51m2 stops
ANA Logo
16:25 - 20:15ORD-SYD
34h 50m1 stop
$1,713ANA
Find Deal
Tue, 7 Oct - Tue, 28 Oct
Air Canada Logo
10:20 - 20:11SYD-ORD
25h 51m2 stops
Air Canada Logo
07:15 - 08:35ORD-SYD
33h 20m3 stops
$1,876Air Canada
Find Deal
Tue, 12 Aug - Tue, 19 Aug
Air Canada Logo
09:20 - 14:54SYD-ORD
20h 34m1 stop
Air Canada Logo
14:08 - 07:20ORD-SYD
26h 12m2 stops
$1,898Air Canada
Find Deal
Sun, 10 Aug - Sun, 24 Aug
American Airlines Logo
09:10 - 06:05SYD-ORD
35h 55m1 stop
American Airlines Logo
15:17 - 06:05ORD-SYD
23h 48m1 stop
$1,974American Airlines
Find Deal
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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 round-trip flight from Sydney to Chicago?

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 February, where tickets cost $1,135 (return) on average. On the other hand, the most expensive months are December and September, where the average cost of round-trip tickets is $2,392 and $1,833 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. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.


Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$813
Best time to beat the crowds (28% less expensive on average)
Most popular time to fly and prices are also 9% 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 $535 for a one-way ticket and $941 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, oneworld, and SkyTeam 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 $1,808 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 $1,626 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 902 reviews
8.5Boarding
8.2Comfort
8.7Crew
7.9Entertainment
7.7Food
Airline reviews

Every leg of the flight was late causing us to miss our flight to Okinawa and have to take the next flight out.

6.0 GoodNancy, July 2025OKA - HND
Read more ANA reviews

Every leg of the flight was late causing us to miss our flight to Okinawa and have to take the next flight out.

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…

Flight delayed by one day and everything was so disorganized by the airline.

All the food seemed to have onions. I don't eat onions. Anyway, everything else was great. The biggest downside was the underpricer company that purchased the tickets from ANA. Underpricer never provided the United Airlines booking number. ANA was a code share and all our flights were on United. I finally was able get booking numbers from Ujuted on X. They saved me from the upsales underwriter tried to saddle my wife and me with.

Overall the experience was ok. My two complaints are that the food is absolutely disgusting. The movies in the flight to Japan were a completely different selection than the ones on the way back. So if you’re looking forward to watching a certain move on the way back, think again.

The staff are very kind ,friendly and helpful .This is my first time flying with ANA and surely will fly again.

Hard to explain because we thought we were booking ANA airlines, not ANA operated via United, so we were disappointed, but for what it’s worth, everything went smooth and loved the movie selections. The food was okay, processed and full of preservatives, so vs what we were expecting with ANA it was different

The overall experience was ok, though there was certainly room for improvement. My husband was asked to check his carry-on bag at the gate due to claims that the flight was “full.” However, upon boarding, we observed ample overhead space and several empty rows of seats. This made the request appear unnecessary and caused some discomfort, particularly as he was the only passenger singled out for this procedure.

The flight was smooth, but there were not enough options for meals and I was given beef when I do not eat beef. The flight going was much better because we received more snacks.

One of the oldest most uncomfortable "lay down" seats I've ever experienced. Old plane and old seats that don't lay flat. The seat back does not even recline - at all. Instead the legrest awkwardly extends to fill the gap between a small cubby into which you must insert your feet/legs. I am 5' 11" and could not lay straight but had to tuck my knees. Ticket was also very expensive. Would not recommend flying business/first on Finair from Melbourne to Bangkok and will not do so again myself.

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

Traditional economy class. Not a full flight so spare seats. Food and drinks were good

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

Inflight entertainment, poor that there are no headrest screens on aircraft used for an international flight.

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

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

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

Touch screens were very difficult to use, generally being laggy and unresponsive- it was quite an art to get it to play the thing you wanted rather than some thing at random. Selection of films and Tv was good when touchscreen decided to finally respond.

Their aircraft are old and amenities lack way behind other international carriers leaving from BNE. Even in economy

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was good. Except Broken looking escape/exit doors over the wings need tending,

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Took off on-time and staff was very nice. Got stuck on tarmac at ATL due to storms, but staff was still wonderful even though they were working and not getting paid.

In a nutshell, my bag, the one I have to pay for, because now you can’t even bring a carry on, did not make it. I am still waiting for an update. The fact that not only were have to pay for it, but on top of that we are stuck without getting it, it’s ridiculous..

The plane was filthy!!!! There were empty food wrappers in the pockets and worst of all a wad of hair where someone had obviously brushed their hair, cleaned out the brush and left the wad of hair in the pocket. It was the most disgusting thing I’ve ever seen!! The seats are so crammed together with NO leg room. The AC vent controllers do not adjust. I will likely not book another AC flight from Florida to Montreal.

This was an excellent experience for a very short flight.

Registered my luggage at 5pm. Arrived at JFK at 1:00 am. Worst trip ever. Never again

Really good, super comfy flight and the stewardess was great.

Air Canada never runs on time. You’re lucky if your flight is not cancelled or diverted. Worst airline in the world for gas lighting its customers.

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