CHI - SYD

$412 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 11/12. 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 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.
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Everything you should know

Cheapest round-trip
$845
Overall average: $1,181
American Airlines
Thu 11/6Sat 11/22
ORD - SYD • 1 stop
Cheapest one-way
$412
Typical prices: $691-$829
Qantas Airways
Wed 11/12
ORD - SYD • 1 stop
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Top airlines
American Airlines
Cheapest • from $845 (round-trip)
ANA
Best reviews • 8.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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 • 11% price drop
March
Most popular
Good to know
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+1
+1
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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

Thu, Nov 6 - Sat, Nov 22
American Airlines Logo
3:00 pm - 9:00 amORD-SYD
25h 00m1 stop
American Airlines Logo
5:45 pm - 11:54 pmSYD-ORD
23h 09m2 stops
$845American Airlines
Find Deal
Sat, Nov 22 - Tue, Dec 30
Qantas Airways Logo
11:40 am - 9:00 amORD-SYD
28h 20m1 stop
Qantas Airways Logo
11:20 am - 4:51 pmSYD-ORD
22h 31m1 stop
$846Qantas Airways
Find Deal
Sat, Nov 8 - Tue, Nov 18
American Airlines Logo
9:35 am - 9:00 amORD-SYD
30h 25m1 stop
American Airlines Logo
11:20 am - 3:55 pmSYD-ORD
21h 35m1 stop
$847American Airlines
Find Deal
Thu, Nov 6 - Sat, Nov 22
Qantas Airways Logo
8:50 am - 9:00 amORD-SYD
31h 10m1 stop
Qantas Airways Logo
11:20 am - 4:48 pmSYD-ORD
22h 28m1 stop
$848Qantas Airways
Find Deal
Tue, Jan 27 - Mon, Feb 2
Air Canada Logo
3:40 pm - 8:40 amORD-SYD
48h 00m2 stops
Air Canada Logo
11:20 am - 2:41 pmSYD-ORD
20h 21m1 stop
$850Air Canada
Find Deal
Sun, Feb 15 - Sun, Mar 1
United Airlines Logo
3:55 pm - 7:00 amORD-SYD
22h 05m1 stop
United Airlines Logo
12:10 pm - 2:45 pmSYD-ORD
19h 35m1 stop
$851United Airlines
Find Deal
Thu, Dec 25 - Thu, Jan 15
Air Canada Logo
3:40 pm - 6:55 amORD-SYD
22h 15m1 stop
Air Canada Logo
11:20 am - 8:00 pmSYD-ORD
25h 40m2 stops
$853Air Canada
Find Deal
Sat, Feb 14 - Wed, Mar 4
United Airlines Logo
6:31 pm - 9:05 amORD-SYD
21h 34m1 stop
United Airlines Logo
12:10 pm - 2:45 pmSYD-ORD
19h 35m1 stop
$854United Airlines
Find Deal
Sun, Apr 5 - Sun, Apr 19
Delta Logo
1:05 pm - 6:35 amMDW-SYD
26h 30m2 stops
Delta Logo
9:25 am - 6:31 pmSYD-MDW
24h 06m2 stops
$1,465Delta
Find Deal
Wed, Dec 31 - Fri, Jan 30
Delta Logo
6:00 am - 8:30 amMDW-SYD
33h 30m2 stops
Delta Logo
10:40 am - 6:34 pmSYD-MDW
24h 54m2 stops
$1,515Delta
Find Deal
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.

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 $1,325 and $1,127 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$412
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 6% 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 $412 for a one-way ticket and $845 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Sydney, with SkyTeam 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 990 reviews
7.9Entertainment
7.7Food
8.2Comfort
8.7Crew
8.6Boarding
Airline reviews

Suite lounge in Honolulu is very exclusive and boarding from the lounge into the plane is unique. First suites were huge and comfortable. Japanese meal is like a high end omakase meal. All the staff were very kind and provided sophisticated service. Fast Track upon landing was appreciated but not needed this time because immigration was so empty and easy.

10.0 Excellentmichael, Sep 2025HNL - NRT
Read more ANA reviews

Suite lounge in Honolulu is very exclusive and boarding from the lounge into the plane is unique. First suites were huge and comfortable. Japanese meal is like a high end omakase meal. All the staff were very kind and provided sophisticated service. Fast Track upon landing was appreciated but not needed this time because immigration was so empty and easy.

I like the service very much. The food just okay but maybe different culture who like, who don't like.

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.

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

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.

After already paying for excess luggage prior to flight, i was advised AT check in that i had to pay $816 or forfeit my flight! The lady at the counter was SO rude and had already started offboarding me when i said i would pay it after asking her three times for the exact amount! Have lodged a formal complaint yet heard nothing. Will not ever travel via Qantas again

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.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

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

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