CHI - SYD

$508 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 6/21. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Chicago to Sydney

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Sydney.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
3:17 pm - 2:40 pmORD-SYD
32h 23m2 stops
 Logo
5:45 pm - 6:51 amSYD-ORD
28h 06m1 stop
$1,158
Find Deal
Thu, Jun 5 - Thu, Jun 12
 Logo
3:17 pm - 2:40 pmORD-SYD
32h 23m2 stops
 Logo
5:45 pm - 6:51 amSYD-ORD
28h 06m1 stop
$1,163
Find Deal
Thu, Jun 5 - Thu, Jun 12
Qantas Airways Logo
6:53 pm - 7:30 amORD-SYD
21h 37m1 stop
Qantas Airways Logo
9:10 am - 9:24 pmSYD-ORD
27h 14m1 stop
$1,349Qantas Airways
Find Deal
Wed, Jul 2 - Wed, Jul 9
Qantas Airways Logo
6:53 pm - 7:05 amORD-SYD
21h 12m1 stop
Qantas Airways Logo
5:45 pm - 11:43 pmSYD-ORD
20h 58m1 stop
$1,353Qantas Airways
Find Deal
Tue, Jul 1 - Tue, Jul 8
Air Canada Logo
10:40 am - 8:20 amORD-SYD
29h 40m2 stops
Air Canada Logo
10:20 am - 8:05 amSYD-ORD
37h 45m3 stops
$1,421Air Canada
Find Deal
Wed, Oct 22 - Wed, Oct 29
American Airlines Logo
6:30 pm - 6:55 amORD-SYD
21h 25m1 stop
American Airlines Logo
5:45 pm - 11:35 pmSYD-ORD
20h 50m1 stop
$1,424American Airlines
Find Deal
Mon, Jun 23 - Wed, Jul 2
Air Canada Logo
10:40 am - 7:20 amORD-SYD
29h 40m3 stops
Air Canada Logo
9:20 am - 8:01 amSYD-ORD
37h 41m3 stops
$1,427Air Canada
Find Deal
Tue, Sep 2 - Wed, Sep 24
American Airlines Logo
6:30 pm - 6:55 amORD-SYD
21h 25m1 stop
American Airlines Logo
9:10 am - 7:29 pmSYD-ORD
25h 19m1 stop
$1,433American Airlines
Find Deal
Wed, Jun 18 - Wed, Jun 25
United Airlines Logo
7:40 pm - 7:00 amORD-SYD
20h 20m1 stop
United Airlines Logo
10:20 am - 12:59 amSYD-ORD
29h 39m1 stop
$1,458United Airlines
Find Deal
Sun, Jun 22 - Mon, Jun 30
United Airlines Logo
7:40 pm - 7:00 amORD-SYD
20h 20m1 stop
United Airlines Logo
9:30 am - 9:10 pmSYD-ORD
26h 40m2 stops
$1,462United Airlines
Find Deal
Wed, Jun 18 - Wed, Jul 9
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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 $864 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $1,507 and $1,340 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonApril
High seasonMarch
Cheapest flight$508
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 17% 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 $508 for a one-way ticket and $1,158 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?

    Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Chicago and Sydney, with oneworld 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 Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Delta. With an average price for the route of $769 and an overall rating of 8.3, ANA is the most popular choice. Delta is also a great choice for the route, with an average price of $948 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.

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.
8.0
DeltaOverall score based on 7936 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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?

Loved the staff. The economy seats could have been bigger.

Airport and crew experience was excellent. We had to queue for the runway - no one’s fault, but it did mean we were 30 minutes late leaving

Overall good experience with flight and airport wheelchair staff. Also got Indian food in the flights

I liked the service, the menu, and the comfort of the seats! Even tho we were seated by the bathrooms, the reclining seats and movie selection was very good, my husband and I didn’t mind at all

Very good as always, stand out airline. The passengers whom choose to stuff baggage that otherwise should be checked-in is a real bother but that's not the airlines doing. A real frustration that passengers just don't want to check-in luggage. This is a pet hate unfortunately.

It’s a two prop flight so I had problems with my ears on re- entering ! But otherwise fine

I love flying with Qantas. There was no onscreen entertaining on this flight, and only a snack provided (not a meal) but still better than Jetstar or Virgin (in my opinion) so still happy.

The food was terrible. And the flight attendants were very rude. One flight attendant wouldn’t help a passenger lift their carry-on. Another flight attendant wouldn’t give a man an extra blanket. And they walked by not even looking at the passengers to see if they needed a glass of water.

Wheelchair assistance to move through the terminals and to/from the plane door was excellent. No vegan snack on the flight, only something with salami and cheese in it.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

I hope these comments will find their way to AC customer experience team. Me and my spouse 50 years of aged coming back from 7 days perfect vacation... While boarding in FLL flight AC1621, one of the boarding agents (tall aged african american) man literelly yeld at my wife during the picture talking process. MAM ! STEP !! BACK !!! We are not illegal immegrants beying deported, nor are we in the millitary. We are customers returning home. This was unacceptable. While boarding in YYZ flight AC1154, one of the boarding agents (tall aged caucasian) man criticied with several complesant remarks my passport condition saying that I could not travel intl with it due to stain, decoloration, and BLOOD. My passport does not have blood on it! Yes it might be in less than perfect condition, but their are ways to talk to customer that does not imply not allow a boarding agent to be angry fathery like, or a custom agent looking at a suspicious individual. Both experience were less than acceptable for might I remind you a paying CUSTOMER returning home.

Short flight so no food or entertainment. Good landing at SFO and on time. We were told no carryon luggage yet lots of people were puting bags in overhead compartments. The rules need to be made more clear. I was on the first leg of an international flight and this is the first time I could not have carryon luggage.

This flight didn't happen for me because of overbooking.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Comfortable seats and movies entertainment available. Better experience than the flight from Toronto to Denver.

Not enough electronic outlets for charging in the Air Canada waiting to board area but the Most important thing….the plane was booked to only 40% capacity and my row of 2 other seats were empty. My row happened to be one of the few rows that did NOT have raising arm rests. The flight attendant made effort to seat me in a different row. I needed wheelchair assistance due to a cyst on my knee and struggled to move from seat to seat to get to the row. Those 2 empty seats tormented me the entire 15+ hour flight as I had to be upright the entire flight and was not able to elevate my knee. Lots of other passengers were laying down due to the arm rest being able to retract. It is a shame that he couldn’t be gracious and find a row that I could move to.

Poor air traffic controller staffing led to a 50%reduction on flights so we got to wait 4 hrs for our flight! Very disorganized at the gate Poor communication with customers

It was delayed by almost 90 minutes and that messed up our plans but it was beyond UA’s control that is what we heard

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