SYD - CHI

$766 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 15/10. 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

Thu, 14 Aug - Thu, 4 Sep
 Logo
13:15 - 22:46SYD-ORD
24h 31m2 stops
 Logo
06:20 - 12:15ORD-SYD
38h 55m2 stops
$1,606
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Fri, 29 Aug - Fri, 12 Sep
 Logo
13:15 - 23:11SYD-ORD
24h 56m2 stops
 Logo
06:20 - 11:45ORD-SYD
38h 25m2 stops
$1,620
Find Deal
Mon, 4 Aug - Mon, 25 Aug
ANA Logo
20:55 - 08:40SYD-ORD
26h 45m1 stop
ANA Logo
20:20 - 19:15ORD-SYD
31h 55m2 stops
$1,712ANA
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Tue, 24 Jun - Tue, 29 Jul
ANA Logo
11:50 - 04:51SYD-ORD
32h 01m2 stops
ANA Logo
17:45 - 19:15ORD-SYD
34h 30m1 stop
$1,721ANA
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Mon, 4 Aug - Mon, 25 Aug
American Airlines Logo
09:10 - 17:42SYD-ORD
23h 32m1 stop
American Airlines Logo
06:00 - 07:05ORD-SYD
34h 05m1 stop
$1,733American Airlines
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Mon, 23 Jun - Fri, 8 Aug
American Airlines Logo
09:10 - 06:38SYD-ORD
36h 28m1 stop
American Airlines Logo
13:40 - 07:05ORD-SYD
26h 25m2 stops
$1,885American Airlines
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Wed, 8 Oct - Thu, 16 Oct
Air Canada Logo
10:20 - 22:07SYD-ORD
27h 47m2 stops
Air Canada Logo
08:55 - 08:20ORD-SYD
31h 25m2 stops
$1,957Air Canada
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Mon, 11 Aug - Thu, 14 Aug
Air Canada Logo
09:20 - 05:38SYD-ORD
35h 18m1 stop
Air Canada Logo
15:35 - 07:20ORD-SYD
24h 45m1 stop
$2,072Air Canada
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Sat, 19 Jul - Wed, 30 Jul
Cathay Pacific Logo
14:05 - 14:25SYD-ORD
39h 20m1 stop
Cathay Pacific Logo
16:00 - 10:50ORD-SYD
27h 50m1 stop
$2,088Cathay Pacific
Find Deal
Thu, 31 Jul - Thu, 7 Aug
Cathay Pacific Logo
14:05 - 14:25SYD-ORD
39h 20m1 stop
Cathay Pacific Logo
16:00 - 20:10ORD-SYD
37h 10m1 stop
$2,223Cathay Pacific
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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.

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 $1,138 (return) on average. On the other hand, the most expensive months are December and September, where the average cost of round-trip tickets is $2,447 and $1,851 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 3 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$766
Best time to beat the crowds (28% less expensive on average)
Most popular time to fly and prices are also 8% 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 $499 for a one-way ticket and $1,046 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?

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

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

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are ANA and Cathay Pacific. With an average price for the route of $1,748 and an overall rating of 8.3, ANA is the most popular choice. Cathay Pacific is also a great choice for the route, with an average price of $2,217 and an overall rating of 7.5.

  • 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.

Top 5 airlines serving 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.
8.3
ANAOverall score based on 882 reviews
7.7Food
8.5Boarding
8.2Comfort
7.9Entertainment
8.7Crew
Airline reviews

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.

6.0 GoodAnonymous, May 2025NRT - SFO
Read more ANA reviews

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.

That food is absolutely disgusting. Bring your own meals because the food not only smells fowl but tastes even more so. Jesus, I’d rather just eat a protein bar.

Everything was great. Wifi was down,but that didn't matter to me.

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.

This was a large plane with an upper deck. It seems like business was upstairs. If it was a US airline then I would say I sat in economy plus, but I think it was just economy. Though since ANA would not allow me to choose seats for the price it may have been plus. Lots of movies to choose from, and good service.

Thankful for the staff who provided blankets cause the plane was quite cold and no way to adjust the airflow in the seats next to the bathroom.

Uh there was a delay, because of the weather. And what took usually an hour flight to Louisville took about 6+ hours. Flight got canceled

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

Airport and crew experience was excellent. We had to queue for the runway - no one’s fault, but it did mean we were 30 minutes late leaving

Overall good experience with flight and airport wheelchair staff. Also got Indian food in the flights

4.5 hr international flight. We got a glass of water. Ranks up there with Ryan Air, Easy Jet, Spirit and Frontier. Expected better.

Gluten free options less explicit on business class, but great service

Very good… seems the virgin staff particularly in the lounge and in flight exceeded expectations.

I liked everything about the experience but would have liked some free snacks!

Crew was great but flight was delayed almost three hours due to a technical issue and we had to go back to the terminal and wait for another one.

Being told why we delayed three hours and not even given an apology by someone. Not a word. Not my airline of choice ever.

Checked Baggage line up was long but moved quickly, rest of the process, boarding, crew was excellent

Virgin has always provided a smooth and comfortable flight. This one was no different. Seats are comfortable. Staff are great. This is my favourite airline.

Virgin changed the flight to an Alliance flight. Smaller plane, tea coffee and water the only refreshments available and not sure what happened to the extra money I paid to sit in a selected seat with extra leg room. This is obviously a regular switch as it happened on our flight there and back. Do not recommend.

Late boarding, late departure due to weather and slow boarding, packed 5+hour flight, only 2 toilets for main cabin, tight leg room, no free food except tea, coffee, and water, arrived 75 minutes late.

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

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

Good flight, friendly crew and overall - good service on United Airlines.

Received email saying that there won’t be a seat back entertainment screen and inflight WiFi would be available. But no WiFi both ways. Say it in the email.

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

flight landed late almost 1.00hr and we 4 passengers missed our connected flight to indianapolis, we need to get the hotel and taxi for the next day flight to home in indianapolis, cost us $ 300 more

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

Good, only discomfort was consistent turbulence through the 3 hour flight. Not sure if in companies control though.

From the kind young lady (w/Vancouver air security) who expedited our check-in to U.S. Customs to the Air Canada gate crew who gave us pre-boarding, the flight attendants who actually offered a strong hand to help me board once I had surrendered my rolling walker at the door, they are all reflections of the thoughtful, genuinely helpful Canadians we have grown to appreciate. Water and other beverages were offered throughout the flight to make sure we weren't dehydrated and the cookie was great. (Husband bought the fruit & crackers snack,) I was delighted to see three movies that I would not have otherwise seen and appreciate that AC left the last film viewable until its conclusion although the flight had actually landed. Last, mahalo to the kind strong gentleman who not offered his hand to help me debark the plane, but gave me an AC pin that I'll truly treasure.

The ground staff was so rude in Toronto airport ...very rude and did not answer simple questions, and made me look like a fool. Very rude ground staff.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

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

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