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SYD - CHI

$913 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 7/8. 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
Sat 15/6
Sat 22/6

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago.
In the last 7 days, travellers have searched 42,211,976 times on KAYAK, and here's why:

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

 
These are the cheapest deals for flights from Sydney to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals from Sydney to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Sydney to Chicago.

Recent one-way flight deals from Sydney to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Sydney to Chicago found on KAYAK recently.

Recent last-minute flight deals from Sydney to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Sydney to Chicago.

Recent direct flight deals from Sydney to Chicago

The latest deals for direct flights from Sydney to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Sydney to Chicago

Find recent round-trip train or bus tickets from Sydney to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
13:15 - 06:24SYD-ORD
32h 09m3 stops
09:19 - 11:45ORD-SYD
35h 26m3 stops
$1,395
Find Deal
Wed, 12 Jun - Wed, 19 Jun
13:15 - 05:49SYD-ORD
31h 34m2 stops
12:32 - 11:45ORD-SYD
32h 13m3 stops
$1,458
Find Deal
Wed, 12 Jun - Wed, 19 Jun
10:20 - 15:34SYD-ORD
20h 14m1 stop
15:40 - 06:55ORD-SYD
24h 15m1 stop
$1,614United Airlines
Find Deal
Mon, 26 Aug - Fri, 13 Sep
10:20 - 15:34SYD-ORD
20h 14m1 stop
16:09 - 07:00ORD-SYD
23h 51m2 stops
$1,620United Airlines
Find Deal
Mon, 26 Aug - Fri, 13 Sep
09:15 - 19:34SYD-ORD
25h 19m1 stop
15:00 - 07:05ORD-SYD
25h 05m1 stop
$1,627American Airlines
Find Deal
Wed, 14 Aug - Wed, 4 Sep
09:15 - 15:36SYD-ORD
21h 21m1 stop
18:25 - 07:05ORD-SYD
21h 40m1 stop
$1,629American Airlines
Find Deal
Wed, 14 Aug - Wed, 4 Sep
20:55 - 05:22SYD-ORD
47h 27m2 stops
17:45 - 09:25ORD-SYD
24h 40m1 stop
$1,665ANA
Find Deal
Wed, 29 May - Tue, 30 Jul
12:25 - 08:20SYD-ORD
35h 55m1 stop
07:10 - 20:15ORD-SYD
44h 05m2 stops
$1,671ANA
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Thu, 31 Oct - Sun, 3 Nov
17:35 - 18:34SYD-ORD
39h 59m1 stop
17:03 - 08:10ORD-SYD
24h 07m1 stop
$1,758Qantas Airways
Find Deal
Tue, 18 Jun - Thu, 25 Jul
08:45 - 21:07SYD-ORD
27h 22m2 stops
15:51 - 07:45ORD-SYD
24h 54m2 stops
$2,129Air New Zealand
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Sun, 8 Sep - Thu, 3 Oct
06:55 - 06:20SYD-ORD
38h 25m3 stops
Wed, 7 Aug
13:15 - 06:00SYD-ORD
31h 45m2 stops
Tue, 20 Aug
17:35 - 06:00SYD-ORD
51h 25m1 stop
$1,009
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Mon, 19 Aug
17:35 - 06:00SYD-ORD
27h 25m1 stop
$1,013
Find Deal
Tue, 20 Aug
16:20 - 23:39SYD-ORD
46h 19m2 stops
$1,016
Find Deal
Sat, 15 Jun
09:15 - 15:55SYD-ORD
21h 40m1 stop
$1,736Qantas Airways
Find Deal
Tue, 18 Jun
10:20 - 14:42SYD-ORD
19h 22m1 stop
$1,800Virgin Australia
Find Deal
Tue, 21 May
20:55 - 05:22SYD-ORD
47h 27m2 stops
$2,414ANA
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Mon, 29 Jul
09:20 - 07:58SYD-ORD
37h 38m3 stops
$2,492Air Canada
Find Deal
Fri, 31 May
08:55 - 19:35SYD-ORD
25h 40m3 stops
$2,853Qantas Airways
Find Deal
Thu, 20 Jun
21:50 - 14:25SYD-ORD
31h 35m1 stop
14:54 - 14:40ORD-SYD
56h 46m2 stops
$2,573
Find Deal
Mon, 20 May - Sat, 25 May
09:20 - 22:04SYD-ORD
27h 44m2 stops
11:00 - 07:20ORD-SYD
29h 20m2 stops
$2,904Air Canada
Find Deal
Mon, 20 May - Sat, 25 May
09:20 - 08:01SYD-ORD
37h 41m3 stops
10:55 - 07:20ORD-SYD
29h 25m2 stops
$2,944Air Canada
Find Deal
Mon, 20 May - Sat, 25 May
09:20 - 08:01SYD-ORD
37h 41m3 stops
10:55 - 07:20ORD-SYD
29h 25m3 stops
$2,953Air Canada
Find Deal
Mon, 20 May - Sat, 25 May
07:35 - 14:25SYD-ORD
45h 50m1 stop
15:40 - 07:20ORD-SYD
24h 40m1 stop
$2,976
Find Deal
Mon, 20 May - Sat, 25 May
07:55 - 22:01SYD-MDW
29h 06m2 stops
09:32 - 06:20MDW-SYD
29h 48m2 stops
$8,130Korean Air
Find Deal
Mon, 20 May - Sat, 25 May
07:35 - 21:00SYD-ORD
28h 25m2 stops
00:30 - 06:15ORD-SYD
38h 45m2 stops
$17,434
Find Deal
Mon, 20 May - Fri, 24 May

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.
If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Sydney to Chicago. For your return ticket, we recommend flying on a Sunday and avoiding Tuesdays for the best deals.

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 February, where tickets cost $1,674 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $2,815 and $2,402 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 2 days before departure. For the absolute cheapest price, our data suggests you should book 35 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 past 3 days, the cheapest one-way tickets to Chicago from Sydney were found on American Airlines ($1,034) and Cathay Pacific ($1,228), and the lowest return tickets were found on United Airlines ($1,614) and American Airlines ($1,627).

Good to know

Low season

February

High season

June

Cheapest flight

$913
Best time to beat the crowds (19% less expensive on average)
Most popular time to fly (14% more expensive 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 $608 for a one-way ticket and $929 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, SkyTeam, and Star Alliance 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, Korean Air or ANA?

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are Korean Air and ANA. With an average price for the route of $1,970 and an overall rating of 8.5, Korean Air is the most popular choice. ANA is also a great choice for the route, with an average price of $1,677 and an overall rating of 8.4.

  • 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 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.

See more FAQs

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.
8.4
ANAOverall score based on 921 reviews
8.3Comfort
8.6Boarding
8.8Crew
8.0Entertainment
7.8Food
Airline reviews

I booked a ANA flight, this was just a regular United flight — as always very bad, dirty, rude service, quite frankly really embarrassing to be flying with this after spending time in Japan.

2.0 MediocreAnonymous, May 2024NRT - EWR
Read more about ANA reviews

I booked a ANA flight, this was just a regular United flight — as always very bad, dirty, rude service, quite frankly really embarrassing to be flying with this after spending time in Japan.

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.

First I will say this was really NOT an ANA flight. ANA used a UNITED jet to perform this flight. I specifically booked with ANA because I did NOT WANT TO FLY UNITED FOR INTERNATIONAL FLIGHTS. So to spend $1800.00 and then discover after booking that it was going to be handled by United was very disappointing. I will be more careful next time when I book. The interior was very cramped in economy class; the dinner meal was terrible and also had extremely small portions for an international flight - the bread roll was ice cold and stale - that salad was very wilted; I’ve never had a “snack” that was so salty that it was difficult to eat; the breakfast “waffle” was practically unrecognizable. Really horrible meals for a very expensive international flight. Bathroom floor was also pretty dirty. I’m hoping my return flight is a real ANA airplane that is cleaned and serviced by ANA personnel with ANA meals. I will never book with ANA again if they continue to use UNITED airline jets. Yuck!!!🤢

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.

I wish the serve should leach and drink. Maybe because only 2hr

All was good, the only thing was it didn't run on time.

Great meal. Best seats ever! They need to teach other airlines how to do that.

Overall excellent but the Captain kept the seat belt sign on for far too long, especially at the beginning and end of the flight. It was 2 hours after take-off before the crew were able to start the service (on an 11 hour night flight, reducing our sleeping time) and the seat belt sign on went on during breakfast (90 mins before landing) and was not turned off again until we landed. This made for an uncomfortable journey of trying to limit fluid intake because it was unclear when the toilets would be available for use.

The staff and crew on board were excellent. Business class however, was very weird. I thought we would have individual pods, but the way it was set up was unexpected. Not very private and If you wanted to lay down, you had to have an entire bed made up for you by the crew, rather than how Delta one works where you could just lie down whenever you feel like it. It was a 16 hour flight. I chose not to have my bed made, and that turned out to be a good idea because everybody who had their bed made had to wait for the crew to roll up their mattresses. So strange!

Food was not good. We asked for Muslim food and it was weird tasteless type of boiled veges.

Couldn’t request a vegan meal somehow but I noticed other people getting them

They announced food service but then never came around. We also couldn’t land so kept trying to get to runway and then had to come up and go around happened like 3 times and cause the child next to me to start throwing up

Good food and entertainment options. Great Staff that were all welcoming and caregiving.

The recline on the seat in front of me came back so that I was staring at the top of the man’s head in front of me the whole trip. He refused to bring his seat back up twice every time he was instructed to do so and only relented when he had a tray of good in front of him. And then right back in my lap!!! Horrible man!! I complained to the staff multiple times, but no one would address the issue. Otherwise, it would have been a perfect flight.

Flight was canceled due to technical issue shortly before the check-in counters opened. Passengers were rebooked on a flight three days later. Request to be accommodated on Air Tahiti Nui could not be processed. Customer service sorted out the refund after calling and being put on hold for almost an hour.

There was nothing I didn’t like, prices a little lower would help

BA Airbus A380 BC upstairs had 2 3 2 layout. The seat was comfy but access for those in middle or window seats had to climb over others fest to get to ailse when seats in bed mode. The layout was not nearly as private as other layouts. The staff was amazing as well as the food. Most airline food is average but this was restaurant quality.

Following a marathon flight riddled by delays and changes from Santiago, Chile, my flight to Melbourne from Sydney was on schedule but I was transferred to the next flight. The reason by ticketing and the floor manager was I missed the entry to flight by one minute! That's right, the emphasised that if I was 1 minute earlier I would be on the flight. I asked what was the point them emphasising 1minute overdue and how that helped me or the situation. They didn't care at all. Replying that if it was one minute earlier they would've done something and smirking delivering the information. Australian's do call Australia home, Qantas calls Australian's suckers.

Qantas are unable to service and unfit for purpose, they cannot transport Australians on time to overseas destinations. On top of the inflated ticketing, the Sydney flight to Santiago was impacted because the plane was delayed arriving and then further bungling by Qantas admitting the ground new ground crew in charge of cleaning were not trained. The impact on passengers with connecting flights was tremendous and long ques of frustrated passengers waiting for rescheduling. **Qantas has become the Australian Spirit of disappointment**

I was pleasantly surprised with my flight to LA with Qantas. Although seats were not the roomies, service was excellent.

The service and smooth landing. Food was delicious and the staff was friendly. We arrived earlier than scheduled.

Wonderful crew, good food. Absolutely loved the wine spritz and wish I could buy it!

Don’t like last minute airline change. Not able to choose seat earlier.

Enjoyed the new possibilities of in flight entertainment. Been awhile since I've flown, and that was a nice surprise. Being able to pick from such a variety was personalized and welcomed.

It's only a short trip from Sydney to Melbourne, which i have done many times. The trip met my expectations

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!

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

My experience was pretty frustrating because the first leg of my flight on United (though booked through Air Canada) was delayed causing me to miss my connecting flight on Air Canada. This could have been an easy solve as there was a direct flight later that morning via Air Canada that they easily could have put me on which would have only gotten me to my destination 2 1/2 hours later but because United and Air Canada don’t seem to have good communication they gave me the run around both telling me to talk with the other which I did three times to no avail. I ended up taking the delayed flight and getting on a new connecting flight which ended up getting me to my destination 6 hours later and I missed the event I was planning to go to this evening.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

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.
7/8Wed
3 stops
38h 25mSYD-ORD
$913
20/8Tue
2 stops
31h 45mSYD-ORD
$980
19/8Mon
1 stop
51h 25mSYD-ORD
$1,009
20/8Tue
1 stop
27h 25mSYD-ORD
$1,013
15/6Sat
2 stops
46h 19mSYD-ORD
$1,016
18/6Tue
1 stopQantas Airways
21h 40mSYD-ORD
$1,736
21/5Tue
1 stopVirgin Australia
19h 22mSYD-ORD
$1,800
29/7Mon
2 stopsANA
47h 27mSYD-ORD
$2,414
31/5Fri
3 stopsAir Canada
37h 38mSYD-ORD
$2,492
20/6Thu
3 stopsQantas Airways
25h 40mSYD-ORD
$2,853

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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.
20/5Mon
multi-stop
31h 35mSYD-ORD
25/5Sat
multi-stop
56h 46mORD-SYD
$2,573
20/5Mon
multi-stopAir Canada
27h 44mSYD-ORD
25/5Sat
multi-stopAir Canada
29h 20mORD-SYD
$2,904
20/5Mon
multi-stopAir Canada
37h 41mSYD-ORD
25/5Sat
multi-stopAir Canada
29h 25mORD-SYD
$2,944
20/5Mon
multi-stopAir Canada
37h 41mSYD-ORD
25/5Sat
multi-stopAir Canada
29h 25mORD-SYD
$2,953
20/5Mon
multi-stop
45h 50mSYD-ORD
25/5Sat
multi-stop
24h 40mORD-SYD
$2,976
20/5Mon
multi-stopKorean Air
29h 06mSYD-MDW
25/5Sat
multi-stopKorean Air
29h 48mMDW-SYD
$8,130
20/5Mon
multi-stop
28h 25mSYD-ORD
24/5Fri
multi-stop
38h 45mORD-SYD
$17,434

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Sydney - Chicago Flights

Departure:

Sydney (undefined)Australia

Return flight deals:

Chicago - Sydney

Cabin classes: