SYD - CHI

$1,058 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 30/4. 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, 0 bags

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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Everything you should know

Cheapest return fare
$1,504
Typical prices: $1,053-$1,152
Air New Zealand
Sun 1/2Sun 8/2
SYD - ORD • 2 stops
Cheapest one-way flight
$1,058
Typical prices: $989-$1,639
Air New Zealand
Thu 30/4
SYD - ORD • 2 stops
Top airlines
Air New Zealand
Cheapest • from $1,620 (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 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 25% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Sun, 1 Feb - Sun, 8 Feb
Air New Zealand Logo
13:55 - 22:59
SYD
-
ORD
26h 04m2 stops
Air New Zealand Logo
13:00 - 08:45
ORD
-
SYD
26h 45m2 stops
$1,504Air New Zealand
Tue, 3 Feb - Mon, 9 Feb
Air New Zealand Logo
11:45 - 20:05
SYD
-
ORD
25h 20m2 stops
Air New Zealand Logo
14:40 - 08:45
ORD
-
SYD
25h 05m2 stops
$1,620Air New Zealand
Fri, 30 Jan - Fri, 6 Feb
Air New Zealand Logo
09:55 - 19:50
SYD
-
ORD
26h 55m2 stops
Air New Zealand Logo
15:53 - 08:45
ORD
-
SYD
23h 52m2 stops
$1,721Air New Zealand
Tue, 3 Mar - Tue, 14 Apr
American Airlines Logo
11:20 - 17:36
SYD
-
ORD
23h 16m1 stop
American Airlines Logo
17:30 - 07:05
ORD
-
SYD
22h 35m1 stop
$1,726American Airlines
Tue, 3 Mar - Tue, 14 Apr
American Airlines Logo
11:20 - 16:38
SYD
-
ORD
22h 18m1 stop
American Airlines Logo
17:02 - 07:05
ORD
-
SYD
23h 03m2 stops
$1,734American Airlines
Tue, 3 Mar - Tue, 14 Apr
American Airlines Logo
14:05 - 18:46
SYD
-
ORD
21h 41m2 stops
American Airlines Logo
17:02 - 07:05
ORD
-
SYD
23h 03m2 stops
$1,744American Airlines
Sat, 16 May - Sat, 6 Jun
Air New Zealand Logo
11:55 - 21:31
SYD
-
ORD
24h 36m2 stops
Air New Zealand Logo
16:40 - 08:45
ORD
-
SYD
25h 05m2 stops
$1,765Air New Zealand
Sun, 1 Mar - Mon, 16 Mar
Multiple Airlines Logo
17:45 - 21:31
SYD
-
ORD
20h 46m1 stop
Multiple Airlines Logo
16:45 - 09:00
ORD
-
SYD
24h 15m1 stop
$1,806Multiple Airlines
Sat, 7 Mar - Sat, 14 Mar
Delta Logo
14:15 - 22:42
SYD
-
MDW
25h 27m2 stops
Delta Logo
13:09 - 07:25
MDW
-
SYD
26h 16m2 stops
$2,229Delta
Tue, 13 Jan - Tue, 20 Jan
Delta Logo
10:40 - 18:32
SYD
-
MDW
24h 52m2 stops
Delta Logo
10:48 - 06:50
MDW
-
SYD
27h 02m2 stops
$2,386Delta
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 February.

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 $1,106 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $2,211 and $1,746 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$1,058
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 12% 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 $1,058 for a one-way ticket and $1,504 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 $2,054 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 $1,608 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 1030 reviews
8.6Boarding
8.7Crew
8.0Entertainment
8.2Comfort
7.8Food
Airline reviews

Although the flight was delayed because of the equipment came in late, I still give them excellent service ..good food selection and in flight entertainment were sufficient.. I will continue to fly with them

10.0 ExcellentAnonymous, Dec 2025
NRT - ORD
Read more ANA reviews

Although the flight was delayed because of the equipment came in late, I still give them excellent service ..good food selection and in flight entertainment were sufficient.. I will continue to fly with them

Staff was rude and loud. No respect for customers unlike the Starflyer Osaka to Haneda sector where service was outstanding. What a stark difference. Maybe United should learn from ANA how to do customer service.

The meals were sufficient and tasty considering it was air travel food. Water coffee and juices offered each time a meal came by and water distributed between meals. It was good service in my opinion. Plenty of movies to enjoy. May not be the one you want but plenty of older movies and plenty of current ones as well. I enjoyed the trip.

we were in premium economy, but we both got middle seats and had to sit separately. i could have avoided this by trying to obtain seats sooner, but i tried 3 times and gave up. ANA's technology is not friendly for newcomers. no, check that---I think it is nigh impossible. not sure we are coming back. ana can do better to provide a front end that's friendly to users in both US and Japan.

Checking in via an alliance partner, even a foreign one should get TSA Precheck printed on your boarding pass. The paper copy issued by ANA didn’t show it. I couldn’t get my digital copy due to some technical issue arising because I checked in with ANA. The kiosks at SFO similarly threw an error. The only way I could have gotten a new copy of my boarding pass was from the UA counter and lines were nearly as long as TSA so I bit the bullet and went through the regular TSA line. If UA wants my business, they need to improve that process.

Flight was diverted to Osaka due to engine problems then arrived at a different airport 6 hours late. We were so tired. ANA did the best they could.

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.

My flying experience was not great. The temperature was ridiculously low. I had a sweater and a big jacket and even then. Since my ticket was an economy ticket, I suppose I didn’t deserve a blanket as they were only available for business. The result, o got a cold I have not been able to shake off in 6 days which has absolutely ruined my stay in Japan as I hasn’t had the chance to leave my hotel room. Everything else that was good, had overshadowed by this. BE A LITTLE MORE HUMAN

Air conditioning was turned to the wrong setting. Way too hot. The entertainment system kept resetting and didn’t work half the flight. Said something to the crew. They didn’t do anything to help. Plane had a mechanical problem that resulted in 2.5 hour delay. Boarded the plane, had to disembark and get back on.

Flight was delayed by 2 hours. Got lucky that i had a long connection, else would have certainly missed my connecting flight. Food is just okay, specially the breakfast is worse . Asked for water 30 mins before landing, the response is that we are landing so everything is packed . I guess traveling in economy that’s what we get. Probably business class passengers would get a different answer. Only good thing is that wifi service is available from auckland to lax for most part Next time will try united or American and then compare.

Good and appreciate the effort Air Zealand puts into using more environmentally friendly food containers and utensils. yay! One of the better airlines for this for sure. Still some bad stuff, but at least Air NZ is trying. :) Also really enjoyed the bluetooth option for personal headsets. :)

I was trying to get confirmation on if my luggage was going to be moved to the earlier flight (I requested standby to get home earlier) and was unable to get help from those working at the counter. The request to be moved to an earlier flight was handled smoothly through the app and appreciate the ease of the request.

They are my favourite airline in the world by a million miles.

Do the bumpy weather the whole trip they were very few times when the seatbelt sign wasn't on

Great except paying $240 usd for 2 pounds over on a checked luggage. Outrageous.

Kayak did not propagate my United miles account and I had to manually get credit.

Like: Aircraft was better than others I've flown in. Crew was great, food was very good. Air New Zealand is now my favorite airline. On our long flight from AKL to YVR there was enough room for those of us in Economy to stretch a bit. My sister is disabled and they took very good care of her and me. Best entertainment offering of all the other airlines. Not so much; Flight from AKL to YRV was delayed BUT they recovered really well so no complaints here. Pretty petty point to complain about. Only negative I have. I will recommend to friends.

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.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

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!

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.