SYD - CHI

$905 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 15/1. 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
$1,515
Typical prices: $1,086-$1,515
Air Canada
Tue 27/1Tue 24/2
SYD - ORD • 2 stops
Cheapest one-way flight
$905
Typical prices: $1,272-$1,883
Multiple Airlines
Thu 15/1
SYD - ORD • 3 stops
Top airlines
Air Canada
Cheapest • from $1,557 (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
Start a new search
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

Tue, 27 Jan - Tue, 24 Feb
Air Canada Logo
11:20 - 22:05
SYD
-
ORD
27h 45m2 stops
Air Canada Logo
15:35 - 09:35
ORD
-
SYD
25h 00m1 stop
$1,515Air Canada
Tue, 27 Jan - Tue, 24 Feb
Air Canada Logo
11:20 - 22:05
SYD
-
ORD
27h 45m2 stops
Air Canada Logo
11:11 - 09:35
ORD
-
SYD
29h 24m2 stops
$1,525Air Canada
Tue, 27 Jan - Tue, 24 Feb
Air Canada Logo
11:20 - 16:42
SYD
-
ORD
22h 22m1 stop
Air Canada Logo
13:05 - 09:35
ORD
-
SYD
27h 30m1 stop
$1,536Air Canada
Wed, 11 Feb - Wed, 18 Feb
Air Canada Logo
11:20 - 14:41
SYD
-
ORD
20h 21m1 stop
Air Canada Logo
07:15 - 09:35
ORD
-
SYD
33h 20m2 stops
$1,557Air Canada
Mon, 9 Feb - Mon, 16 Feb
Air New Zealand Logo
13:55 - 20:25
SYD
-
ORD
23h 30m2 stops
Air New Zealand Logo
14:33 - 08:45
ORD
-
SYD
25h 12m2 stops
$1,598Air New Zealand
Mon, 9 Feb - Mon, 16 Feb
Multiple Airlines Logo
11:20 - 22:19
SYD
-
MDW
27h 59m2 stops
Multiple Airlines Logo
06:00 - 09:00
MDW
-
SYD
34h 00m2 stops
$1,953Multiple Airlines
Fri, 16 Jan - Fri, 30 Jan
Delta Logo
10:40 - 22:07
SYD
-
MDW
28h 27m2 stops
Delta Logo
13:26 - 08:30
MDW
-
SYD
26h 04m2 stops
$2,164Delta
Mon, 9 Feb - Mon, 16 Feb
Delta Logo
10:40 - 17:29
SYD
-
MDW
23h 49m2 stops
Delta Logo
13:49 - 08:30
MDW
-
SYD
25h 41m2 stops
$2,366Delta
Fri, 16 Jan - Fri, 30 Jan
Multiple Airlines Logo
14:05 - 16:23
SYD
-
MDW
19h 18m1 stop
Multiple Airlines Logo
17:01 - 06:55
MDW
-
SYD
44h 54m2 stops
$3,799Multiple Airlines
Wed, 11 Feb - Wed, 18 Feb
WestJet Logo
20:30 - 09:54
SYD
-
MDW
30h 24m2 stops
WestJet Logo
10:49 - 06:35
MDW
-
SYD
50h 46m2 stops
$9,121WestJet
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 January.

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 $1,089 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $2,040 and $1,719 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$905
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 11% 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 $905 for a one-way ticket and $1,515 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 $2,022 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 $1,582 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 1049 reviews
7.7Food
8.2Comfort
8.7Crew
8.5Boarding
7.9Entertainment
Airline reviews

Good airlines btu ORL airport messed up the return flight for me. Checking out a connecting flight pax is unacceptable.

8.0 Excellentjbritto, Dec 2025
HND - ORD
Read more ANA reviews

Good airlines btu ORL airport messed up the return flight for me. Checking out a connecting flight pax is unacceptable.

The pilot was kept warning about the weather terrifying us. The flight attendants were not warm or pleasant.

I couldn’t sit with my daughter. we are separate and both seat was not window or halway side. in the middle. if we sit together will be share comfort seat and more easy travel. this is bad.

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.

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.

Entertainment screen froze and had to be reset. Noticed it happened to other passengers as well.

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.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

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.

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

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

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!

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

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.