CHI - SYD

$492 Find Cheap Flights from Chicago to Sydney

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Sydney departing on 1/17. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Sydney

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Sydney (CHI-SYD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Sydney 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 round-trip flight deals from Chicago to Sydney

Mon, Oct 27 - Sun, Nov 9
Multiple Airlines Logo
12:03 pm - 9:00 amMDW-SYD
28h 57m2 stops
Multiple Airlines Logo
2:05 pm - 10:03 pmSYD-MDW
24h 58m2 stops
$1,033Multiple Airlines
Find Deal
Mon, Oct 20 - Sun, Nov 2
Multiple Airlines Logo
9:44 am - 8:05 amMDW-SYD
30h 21m2 stops
Multiple Airlines Logo
2:05 pm - 11:03 pmSYD-MDW
24h 58m2 stops
$1,072Multiple Airlines
Find Deal
Mon, Feb 16 - Sun, Mar 1
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
ANA Logo
12:25 pm - 8:54 amSYD-ORD
37h 29m2 stops
$1,129ANA
Find Deal
Tue, Feb 17 - Tue, Mar 3
Hawaiian Airlines Logo
2:00 pm - 7:45 pmORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
9:40 pm - 1:04 pmSYD-ORD
32h 24m2 stops
$1,135Hawaiian Airlines
Find Deal
Thu, Feb 19 - Sun, Mar 1
Hawaiian Airlines Logo
2:00 pm - 7:45 pmORD-SYD
36h 45m2 stops
Hawaiian Airlines Logo
9:40 pm - 5:04 amSYD-ORD
24h 24m2 stops
$1,173Hawaiian Airlines
Find Deal
Tue, Feb 17 - Tue, Mar 3
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
ANA Logo
12:25 pm - 5:16 amSYD-ORD
33h 51m2 stops
$1,197ANA
Find Deal
Sat, Feb 28 - Fri, Mar 6
Fiji Airways Logo
4:45 pm - 12:30 pmORD-SYD
26h 45m2 stops
Fiji Airways Logo
2:10 pm - 11:57 pmSYD-ORD
26h 47m2 stops
$1,233Fiji Airways
Find Deal
Sun, Jan 25 - Sat, Jan 31
Fiji Airways Logo
5:40 pm - 12:30 pmORD-SYD
25h 50m2 stops
Fiji Airways Logo
2:10 pm - 7:20 pmSYD-ORD
22h 10m2 stops
$1,275Fiji Airways
Find Deal
Sun, Nov 16 - Tue, Dec 9
Delta Logo
1:47 pm - 8:30 amMDW-SYD
25h 43m2 stops
Delta Logo
10:40 am - 11:32 pmSYD-MDW
29h 52m2 stops
$1,467Delta
Find Deal
Sat, Nov 22 - Tue, Dec 9
Delta Logo
7:02 pm - 8:30 amMDW-SYD
44h 28m2 stops
Delta Logo
10:40 am - 11:32 pmSYD-MDW
29h 52m2 stops
$1,485Delta
Find Deal

Everything you should know

Top airlines
ANA
Cheapest • from $1,129 (round-trip)
ANA
Best reviews • 8.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Video guide: How to find cheap flights to Sydney
Watch video
Watch video
Watch video
Watch video
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 12% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$1,033
Multiple Airlines
Mon 10/27Sun 11/9
MDW - SYD • 2 stops
Cheapest one-way
$492
Typical prices: $418-978
Multiple Airlines
Sat 1/17
ORD - SYD • 2 stops
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Sydney!
Booking Insights

KAYAK's insights & trends for Chicago to Sydney flights

Get data-powered insights and trends into flights from Chicago to Sydney to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to Sydney
Find cheap flights to Sydney

Planning a trip from Chicago to Sydney? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

How much is a round-trip flight from Chicago to Sydney?

What’s the cheapest day of the week to fly from Chicago to Sydney?

The average price of all round-trip flights from Chicago to Sydney clicked on KAYAK for each day over the last 12 months.

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

What is the cheapest month to fly from Chicago to Sydney?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Sydney, 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 Chicago to Sydney is August, where tickets cost $851 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $1,372 and $1,099 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Sydney, 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 Chicago to Sydney, you should book around 3 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$492
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to Sydney

When to book flights from Chicago to Sydney

Are your dates flexible? Find out the best times to travel from Chicago to Sydney 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 Chicago to Sydney

  • Can I fly directly from Chicago to Sydney?

    Unfortunately, there aren’t any airlines with a direct connection from Chicago to Sydney. Your trips will involve at least one layover, with certain airlines even having two layovers scheduled for this trip. The location of the layover will depend on the airline you’re flying with. For instance, Air New Zealand has its layovers scheduled for Auckland while Air India has Delhi. Both American Airlines and United have Los Angeles as the set layover destination for this route.

  • Is public transport available from Sydney Airport (SYD) to downtown Sydney?

    Yes, there is a train that connects the airport to the city center. It is the cheapest option available and also the quickest, taking the best part of fifteen minutes between the airport and downtown. However, it is not as convenient as a taxi especially when you have a lot of luggage as it will drop you off at the Circular Quay in the center of Sydney then you will have to walk to your hotel.

  • What are the benefits of upgrading to first class for this trip?

    For a long flight like this one, you are sure to get maximum value for your money when you upgrade to first class. The seats are much more comfortable, making the trip more bearable, and you can stretch out freely with the extra legroom. In addition, you will be served an amazing selection of meals and drinks to enjoy at various points during the flight. Lastly, you will be able to access the first-class lounges during your layover, where you can freshen up and get some rest while waiting for the second leg of the flight.

  • Do I need a visa to fly from Chicago to Sydney?

    Yes, a visa is one of the mandatory requirements for all US citizens going to Sydney or any other Australian city. As they don’t provide any visas on arrival, you have to apply beforehand by visiting the Embassy or Consulate in advance of your travel dates to ensure that they have been processed by the time you’re flying out. You can also apply for an ETA via an online process, which is much more convenient.

  • What is the cheapest flight from Chicago to Sydney?

    In the last 3 days, the lowest price for a flight from Chicago to Sydney was $492 for a one-way ticket and $1,033 for a round-trip.

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

    Yes, you’ll need a passport to travel to Sydney from Chicago.

  • Which airports will I be using when flying from Chicago to Sydney?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Sydney Kingsford Smith is the only airport in Sydney. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Sydney?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Sydney?

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

  • What is the most popular layover when flying to Sydney from Chicago?

    Los Angeles is the most popular layover city among KAYAK users traveling from Chicago to Sydney.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Fiji Airways. With an average price for the route of $1,143 and an overall rating of 8.4, ANA is the most popular choice. Fiji Airways is also a great choice for the route, with an average price of $1,227 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to Sydney?

    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 Chicago to Sydney.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Sydney?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sydney from Chicago 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 Chicago to Sydney?

    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 Sydney with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Sydney?

    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 Sydney from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Sydney

  • Air New Zealand is a great option to book when flying with the entire family. They have free Wi-Fi available plus seatback on-demand video and free meals, all of which should make it a better experience for the kids.
  • The Blue Line train from downtown Chicago to O’Hare International Airport (ORD) is a good commuter option when you want to avoid the rush hour traffic that is usually quite a menace.
  • United Airlines doesn’t allow passengers to bring carry-on bags to the economy class cabin. However, they do allow one checked bag for free, meaning if you have any bags, you will need to check them before the flight.
  • American Airlines offers travelers the chance to calculate and offset the emissions generated during the flight from Chicago to Sydney through Cool Effect. This is a great way to make your trips more sustainable and keep the carbon footprint low.
  • Chicago Midway is an alternative departure airport to O’Hare. It is closer to downtown Chicago and also less busy, however, there are few flight options from the airport with all of them being served by Delta and including at least two layovers.

Reviews of the top 5 airlines serving from Chicago to Sydney

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sydney. 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 Chicago to Sydney? 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 963 reviews
8.6Boarding
8.7Crew
7.9Entertainment
7.7Food
8.2Comfort
Airline reviews

Warm the bread. Movies: better choices to include Chinese movies options or some of the older winners of flim festival

8.0 ExcellentAnonymous, Sep 2025HNL - NRT
Read more ANA reviews

Warm the bread. Movies: better choices to include Chinese movies options or some of the older winners of flim festival

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.

Flight was on an ANA flight not air Japan. They did most excellent. Again the flight had excellent legroom for someone that is over 6 foot tall and the staff was very very nice. The only issue you may run into is that the person sitting next to you, may not be able to speak the same language as you.

The crew was very nice and polite. They made sure everybody got their meal and drinks. Even the economy class had a very adequate leg room for someone that is over 6 foot tall.

Purchased WiFi was slow to non functional. Staff was not personable or friendly. Seats were cramped. Boarding took long but I expected that.

Luckily I just tried to sleep. But the entertainment system was awkward to operate. I hate all this stuff with apps and adding it to your phone and all. It is a nuisance. I would prefer a good magazine or newspaper in the pocket in front of me or available.

The seats are uncomfortable. The flight attendants are not pleasant. They do their job, but not with a ray of sunshine and warmth. The food was awful, not what I would expect from an Asian airline. All of the other Asian airlines I have flown have far better food. The food was on par with United airlines food, which is really bad. Maybe ANA should get out of the alliance with United.

One of the best 14 hour flights I've ever had. Crew was friendly throughout which can be difficult on longer flights. The crew being kind and respectful is very important for me. Plane felt clean and I was able to get some well needed uninterrupted sleep. I put them slightly above Cathay Pacific as far as cleanliness the only down side was a lack of entertainment selections, but hey I am an American taking a trip on a Japanese airline so I cannot complain. Thank you ANA and the Tokyo airport all very friendly. Will see you soon

Poor. We weren’t able to check in online (for several hours until we gave up) for no apparent reasons although our passports were loaded successfully. When we were at the airport check-in, a rep helped us at the kiosk but she disregarded the KTN provided to her so we had to come back for it after being questioned by the TSA person…

A few more inches of legroom is all i ask

One of the best Qantas business flights I've had. Quality product

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.

Airline running better than post Covid, proper boarding process now implemented, some aircraft feeling a bit old and tired, crew fine, online experience better.

Five hour flight instead of four hours due to westerly headwinds which wasn’t the fault of Qantas !

The wifi was out. Otherwise it was great flight. Richard, as CSM, was excellent.

Was bumped to a later flight because of inefficiency on part of the airline.

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?

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

Bad food, small seats that didn’t recline. I thought I was buying a quantas ticket so I feel like I got scammed

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Worst seats I’ve ever had !!! The seats were very narrow and uncomfortable and misaligned with the seats in front of mine leading to bottom of the seat in front of mine pressing on my legs for 15.5 hours !

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

For the price, it was a really good experience. There was no entertainment on board, so I couldn't really rate this, and I didn't order a meal. I appreciated that there was a free glass of wine.

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

I think overall both Air Canada and Air New Zealand did a good job the their flights. It is nice to have movies, music, podcasts etc to watch for the long flights. Just wish the seats were wider and had a foot rest to change my leg positions during the trips.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.