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SYD - CHI

Find cheap flights from Sydney to Chicago from $639

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 9/17. 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
0 bags
Sat 6/1
Sat 6/8

Search 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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Cheap flight deals from Sydney to Chicago (SYD-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
9:15 am - 5:10 pmSYD-ORD
22h 55m1 stop
11:55 am - 7:05 amORD-SYD
28h 10m1 stop
$1,060British Airways
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Thu, May 30 - Wed, Jun 12
9:15 am - 12:16 amSYD-ORD
30h 01m1 stop
8:25 am - 8:10 amORD-SYD
32h 45m1 stop
$1,075American Airlines
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Thu, Jun 13 - Mon, Jul 15
1:15 pm - 6:00 amSYD-ORD
31h 45m2 stops
1:13 pm - 11:45 amORD-SYD
31h 32m3 stops
$1,204
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Wed, May 15 - Wed, May 22
8:55 pm - 5:26 amSYD-ORD
47h 31m2 stops
5:45 pm - 9:25 amORD-SYD
24h 40m1 stop
$1,211ANA
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Sat, Jun 15 - Sun, Jul 14
1:15 pm - 6:40 amSYD-ORD
32h 25m3 stops
1:13 pm - 11:45 amORD-SYD
31h 32m3 stops
$1,238
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Wed, May 15 - Wed, May 22
9:20 am - 7:58 amSYD-ORD
37h 38m3 stops
8:45 am - 7:20 amORD-SYD
31h 35m2 stops
$1,302Air Canada
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Thu, May 30 - Fri, Jun 7
9:20 am - 7:58 amSYD-ORD
37h 38m3 stops
8:45 am - 7:20 amORD-SYD
31h 35m3 stops
$1,308Air Canada
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Thu, May 30 - Fri, Jun 7
8:15 am - 9:10 amSYD-ORD
39h 55m1 stop
12:05 pm - 6:10 amORD-SYD
27h 05m1 stop
$1,409Japan Airlines
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Tue, Sep 10 - Sat, Sep 14
11:50 am - 5:33 amSYD-ORD
32h 43m2 stops
7:35 pm - 7:15 pmORD-SYD
56h 40m2 stops
$1,410ANA
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Tue, Sep 10 - Sat, Sep 14
8:15 am - 12:16 amSYD-ORD
55h 01m2 stops
8:16 am - 6:10 amORD-SYD
30h 54m2 stops
$1,682Japan Airlines
Find Deal
Sun, Jun 16 - Thu, Jun 27

Flights from Sydney to Chicago - Travel Insights & Trends

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 flights from Sydney to Chicago clicked on KAYAK for each day over the last 12 months.
For Sydney to Chicago, Saturday 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 Tuesday, with Friday 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 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 October, where tickets cost $1,297 on average. On the other hand, the most expensive months are December and January, where the average cost of tickets is $2,042 and $1,961 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Sydney to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.

Which airlines provide the cheapest flights from Sydney to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Sydney to Chicago were found on British Airways ($1,060) and American Airlines ($1,075). Cathay Pacific proposed the cheapest one-way flight at $836.

Good to know

Low season

January

High season

June

Cheapest flight

$639
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Sydney to Chicago Midway 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 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 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 $639 for a one-way ticket and $1,060 for a round-trip.

  • Do I need a passport to fly between Sydney and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Sydney and on arrival in Chicago.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are ANA and United Airlines. With an average price for the route of $1,115 and an overall rating of 8.4, ANA is the most popular choice. United Airlines is also a great choice for the route, with an average price of $1,737 and an overall rating of 7.4.

  • 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 round-trip 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.

See more FAQs

Top 4 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.
8.4
ANAOverall score based on 944 reviews
8.0Entertainment
8.6Boarding
8.8Crew
8.3Comfort
7.8Food
Airline reviews

Staff and crew are wonderful, professional and courteous. Meal is delicious and snacks can be improved. Entertainment needs improvement, pls update selections of movies. I appreciate that our flight was on time

8.0 ExcellentTheresa, Apr 2024NRT - HNL
Read more about ANA reviews

Staff and crew are wonderful, professional and courteous. Meal is delicious and snacks can be improved. Entertainment needs improvement, pls update selections of movies. I appreciate that our flight was on time

I flew economy class so of course it’s not as roomy as business and first class. But overall it was ok and the seat had an interesting way to recline — the seat itself extended forward instead of the backrest. This way the person sitting behind me would not lose space by my reclining—excellent concept. I wish all airlines used these seats.

Flying with ANA is always a breeze. Seats are very comfortable.

For the price of a seat that is obviously crammed together so as to get many more people onboard and combined with the long flight duration, Free WiFi should be an automatic “Thank You for Flying with Us!” To charge an additional fee when so many other businesses offers it is a bit “cheap” on the airline’s part.

Ticket was purchased as a United Airlines flight (operated by All Nippon) like what does that even mean? Makes for a VERY confusing flight experience. For instance, what do I look for a United drop off signage and ticket counter or ANA? No explanation anywhere to be found. I also felt a little bit scammed by the obsurdely restrictive seat selection provided. Only middle seats available!! Are you kidding me!! On 6hr + 10hr flights you're forcing me into the middle seat without telling me before I purchased the ticket?? This should be illegal. And to top it off, on the Tokyo LA leg there were quite a few empty seats including window seats! I must also say, the food was a dissappointing as well for my taste, fish with rice ( mostly plain white rice) or a vegetable medly for the breakfast meal? Should be at least 4 choices and at least 1 with eggs. Outside of these issues flight was otherwise ok.

It was very nice. I was a bit disappointed by the few meal services. There were probably more drink services that I missed while sleeping, but I would have liked the crew to bring more than one drink service before landing and to bring more than one drink service and coffee service after take off

Food was high quality. Crew was extremely professional, polite, attentive. Flights were on time. Plane had good media tech.

It was ok I thought because my flight was 1pm i was expecting to have lunch but it didn’t and after 7 hr finally dinner time was only chicken sandwich and next breakfast was an hour before plane land in Tokyo. so I should bring some food with me. Japanese flight attend was nice but the other was chewing gum and how she ask and respond to customers was not professional I felt. Maybe because Japan flight attendant is highly train and everyone looked very dress and professional so I was kind disappointed. I like that the bathroom was very clean .

Lovely airport at Haneda. Great food selection. Spacious and private boarding area with dedicated bathroom for each gate.

They did not get my request for veg food that i made a month ago. Also did not have any backup veg food on board or fruit plate or simething. Very disappointing as i had hward about how grwat ANA was supossed to be. Alsio entertainment was lacking and screen and tech was subpar. Overall just mid to low tie. They are living off reputation and are being passed up by most other carriers.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

I was appalled to have to pay for just a regular seat when I went to book 24 hrs before my flight! Because it was only an hour flight I didn’t choose a seat from Grand Junction to Denver, but I did for Toronto and had to pay just to choose a regular available seat! In my 60+ years of flying this was the first time I have heard of this. Also, allowing people to bring on “huge “ suitcases, not carry on size, but much bigger, and then a large pack pack stuffed. So they take up all the room in the overhead bins and if we are later boarding, there is no room so we have to check our small carry on. I have already paid for and checked in one bag! I certainly will not choose to fly with United again unless it is the “only” airline available!

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Fresh fuit or veg snacks would be so great, but there are two good restaurants in Denver airport. Try Etais UDIS or Freshens DIA for nutritious delicious pita sandwiches/ donairs and crepes in Freshens.

Crowded plane but it flew on time and had friendly staff

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

The Air Canada agent was very helpful helping with my luggage and cat carrier when I went there instead of United.

Book cheap flights from Sydney to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Sydney to Chicago found on KAYAK in the last 72 hours.
9/17Tue
2 stops
40h 04mSYD-MDW
$639
5/14Tue
3 stops
48h 15mSYD-ORD
$653
5/12Sun
3 stops
45h 10mSYD-ORD
$659
10/16Wed
1 stopCathay Pacific
32h 05mSYD-ORD
$836
5/13Mon
1 stopCathay Pacific
31h 35mSYD-ORD
$841
7/2Tue
1 stopUnited Airlines
29h 29mSYD-ORD
$1,193
5/14Tue
1 stopUnited Airlines
29h 29mSYD-ORD
$1,194
5/31Fri
3 stopsAir Canada
37h 38mSYD-ORD
$1,367
5/12Sun
1 stopANA
42h 05mSYD-ORD
$3,931
5/7Tue
1 stopANA
35h 50mSYD-ORD
$4,021

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Last minute flights from Sydney to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Sydney to Chicago that are departing in the next 10 days.
5/5Sun
multi-stopANA
35h 50mSYD-ORD
5/12Sun
multi-stopANA
35h 15mORD-SYD
$1,209
5/5Sun
multi-stopANA
32h 34mSYD-ORD
5/12Sun
multi-stopANA
35h 15mORD-SYD
$1,530
5/5Sun
multi-stopAmerican Airlines
35h 00mSYD-ORD
5/12Sun
multi-stopAmerican Airlines
28h 40mORD-SYD
$1,843
5/5Sun
multi-stopChina Southern
47h 35mSYD-ORD
5/12Sun
multi-stopChina Southern
35h 34mORD-SYD
$1,872
5/5Sun
multi-stopDelta
23h 34mSYD-MDW
5/12Sun
multi-stopDelta
26h 53mMDW-SYD
$2,003
5/5Sun
multi-stop
39h 03mSYD-ORD
5/12Sun
multi-stop
32h 11mORD-SYD
$2,324
5/5Sun
multi-stop
52h 56mSYD-MDW
5/12Sun
multi-stop
29h 49mMDW-SYD
$2,965

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Sydney - Chicago Flights

Departure:

Sydney (SYD)Australia

Return flight deals:

Chicago - Sydney

Cabin classes: