CHI - SYD

$486 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 8/11. 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
$1,069
Multiple Airlines
Mon 8/24Tue 9/8
MDW - SYD • 3 stops
Cheapest one-way
$486
Typical prices: $831-$925
Multiple Airlines
Tue 8/11
ORD - SYD • 2 stops
Top airlines
Cheapest • from $1,195 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Sydney. You'll need at least 1 connection.
Insights
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Insights
Top layover airports
Cheapest • Avg $238 (round-trip)
Shortest trip • 14h 05m (one-way)
Insights
Insights
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When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 64% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Start a new search
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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, Aug 24 - Tue, Sep 8
Multiple Airlines Logo
6:05 am - 11:50 am
MDW
-
SYD
38h 45m
3 stops
Multiple Airlines Logo
6:15 am - 10:58 am
SYD
-
MDW
43h 43m
3 stops
$1,069Multiple Airlines
Mon, Aug 24 - Tue, Sep 8
Multiple Airlines Logo
9:20 am - 11:50 am
ORD
-
SYD
35h 30m
3 stops
Multiple Airlines Logo
6:15 am - 6:17 am
SYD
-
ORD
39h 02m
2 stops
$1,073Multiple Airlines
Mon, Aug 24 - Tue, Sep 8
Multiple Airlines Logo
9:20 am - 11:50 am
ORD
-
SYD
35h 30m
3 stops
Multiple Airlines Logo
6:15 am - 11:55 pm
SYD
-
ORD
56h 40m
3 stops
$1,077Multiple Airlines
Sun, Aug 16 - Sat, Aug 29
ANA Logo
5:45 pm - 7:10 pm
ORD
-
SYD
34h 25m
1 stop
ANA Logo
11:45 am - 4:45 am
SYD
-
ORD
32h 00m
2 stops
$1,195ANA
Sun, Aug 16 - Sat, Aug 29
ANA Logo
5:45 pm - 7:10 pm
ORD
-
SYD
34h 25m
1 stop
ANA Logo
11:45 am - 2:55 pm
SYD
-
ORD
42h 10m
1 stop
$1,202ANA
Tue, Aug 11 - Wed, Aug 19
Multiple Airlines Logo
9:13 pm - 11:50 am
ORD
-
SYD
47h 37m
2 stops
Multiple Airlines Logo
5:50 pm - 5:59 am
SYD
-
ORD
27h 09m
1 stop
$1,208Multiple Airlines
Tue, Oct 13 - Sat, Oct 24
Delta Logo
9:30 am - 7:50 am
MDW
-
SYD
30h 20m
2 stops
Delta Logo
10:15 am - 4:50 pm
SYD
-
MDW
22h 35m
2 stops
$1,610Delta
Sat, Aug 22 - Fri, Sep 4
Delta Logo
1:25 pm - 6:50 am
MDW
-
SYD
26h 25m
2 stops
Delta Logo
9:15 am - 6:33 pm
SYD
-
MDW
24h 18m
2 stops
$1,611Delta
Thu, Aug 13 - Thu, Aug 27
Delta Logo
12:46 pm - 6:50 am
MDW
-
SYD
27h 04m
2 stops
Delta Logo
9:15 am - 6:01 pm
SYD
-
MDW
23h 46m
2 stops
$1,612Delta
Sat, Aug 22 - Fri, Sep 4
Delta Logo
1:25 pm - 6:50 am
MDW
-
SYD
26h 25m
2 stops
Delta Logo
9:15 am - 6:01 pm
SYD
-
MDW
23h 46m
2 stops
$1,613Delta
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Sydney departing in August.

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 May, where tickets cost $142 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is $831 and $793 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 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$486
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 25% increase in price.
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 5 days, the lowest price for a flight from Chicago to Sydney was $486 for a one-way ticket and $1,069 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 Air New Zealand?

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Air New Zealand. With an average price for the route of $1,256 and an overall rating of 8.3, ANA is the most popular choice. Air New Zealand is also a great choice for the route, with an average price of $1,508 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.
7.8
DeltaOverall score based on 8453 reviews
7.2Food
7.8Entertainment
8.1Boarding
7.8Comfort
8.5Crew
Airline reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

2.0 MediocreJean, Jun 2026
MDW - ATL
Read more Delta reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

It was very cold because the air conditioner was on high power, and my son got sick.

PREMIUM ECONOMY - excellent !Brilliant new plane. Excellent tv catalogue. Good food. Good communication and service from all friend Australian crew. Good communication from captain. Best travel experience in years.

I couldn't hear all of the announcements. It was nice when they put them on the screen.

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

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.

Delayed and missed connection, was not re-booked like other travelers so ended up being stuck for several hours due to no one handling my booking.

same as previous comments. i hate being on a plane that long. no problems w/anything else.

Much better than I expected for such a long flight.

Good - better than other airlines in terms of food and seat comfort.

Experience was great. My only advice is to have a pasta dish on the menu. Otherwise everything was excellent.

Flight LA to Sydney was first moved earlier by 2 hrs from 10:25 pm to 8:25pm roughly a week before departure. Then on actual departure date, it was delayed 2x, and needed up leaving close to 10 pm. Then entertainment for the whole flight wasn’t working for most of the seats including ours. The baby crib at the middle isle was being taped to the wall to keep it tacked in using a packing tape while passengers were walking by looking for their seats. Not projecting good confidence. After a few minutes after take off the whole crib fell off. Good the people seating next to it wast hit or got scared. At arrival at Sydney, crew handed the customs forms as we were getting out of the plane. So passengers had to scramble to find a place to fill up the forms along the corridor going to immigration. So no one is available to help from Qantas to fill up the entry forms. Not a very good experience for a flagship carrier.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Smooth flight. As always dinner could have been more generous. Breakfast was great.

Moody attendants that can barely look up at the passengers. I’m all for people having an off day, but you can tell some Untied Airlines Employees have lost their zeal for their jobs

Great checkin experience and flight crew were very friendly and helpful

Staff did not care, and very clearly did not want to be serving passengers. Requests were ignored repeatedly. Toilets filthy. Bins were just trash bags hung around the place that were never emptied. It was a challenge to even get a glass of water on a 14 hour flight.

Got automatically assigned a middle seat, unless I fork out extra money for seat assigment.

Flight was diverted to Canberra because Not enough fuel to circle on Sydney’s skies waiting for showers to pass. After that everything went wrong. It took forever to put fuel. Once back rolling, we stopped short of takeoff because crew had reached maximum work hours per shift. Back to gate we waited and waited in the plane with no water and no food - a total of 4 hours. Received contrasting news about the follow up of our trip. Finally we disembarked but our luggage could not be processed there as not enough custom agents. We ended up on buses and arrived at Sydney airports after a 3 hours trip. There we had to queue in line with 240 more passengers to file a lost luggage claim. We received the luggage after 48 hours, many of which spent holding with non-existent United customer service. Never able to speak to an actual person during those long phone calls. Finally on a chatline I could talk to a baggage agent, who filed another report as our luggage did not appear anywhere in their system. Thus it was surprising to get it back.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

I was traveling alone abroad for the first time and the staff was not helpful and rude at times.

Baggage allowances are terrible and the experience of only being allowed one bag and paying so much to take sporting equipment to a known ski area should be addressed.

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

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 !

Crazy seating issues. We got seated far apart. Offered middle seats at a premium rate. Why is a middle seat now the expensive seat? Baffling.

The food at Admirals Club was really great Pijamas were a nice feature The flight attendant was very nice and great attitude The aa.com does not work well specially internet service Overall a very good flight .

Flight a little late. Entertainment system didn’t work for first hour. Toilets dirty after 2 hours. Is there no one assigned to clean them?

I'm 6'8" (2.03m) so more legroom would alwqys be appreciated, especially on long international flights. The food choices were underwhelming.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

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.

Terrible. My brother broke his leg and couldn’t board the flight and air Canada couldn’t do anything about rescheduling his flight. Poor customer service and help all around

I Teall staff was great and helpful and communicated needs and special care for my granddaughters and family as well as others. Well done

Terrible experience! All flights delayed, staff had no idea of what they were doing, and at the end luggage lost for 2 days!

Flight delayed 3 times and also delayed again and by the time I reached Sydney, I couldn't get my Virgin Air as my flight was delayed and I was asked to contact here and there and asked to go to this and that terminal and was told there's no other flight as flights are all full to Melbourne. Thank God, at the very last minute, I was put into Qantas and didn't arrive till 7.30 pm in Melbourne instead of 2 pm. Will never use Air Canada again. Besides, the sittings is so tight and can hardly stretch a bit and eat without elbowing my side passengers. It was indeed a very uncomfortable flight.

Crew helped to find more comfortable seats for passengers. We never got tea or coffee on this trip even when we asked. Not even with breakfast.

I could feel the knees of the person behind me in my lower back for 15 1/2 hours. The. Seats were small and space was tight. People were nice. Coffee in the morning was in a small cup and half full and they never came around again.

THEY LOST MY BAGS. I WILL NOT GET THEM BACK FOR 2 WEEKS. everything was delayed. boarding, take off, everything. it was horrible. i am now without luggage for 2 weeks and they have offered me 0 compensation or help. i will NEVER fly air canada again and i suggest you don’t either <3

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

Information on your arrival and departure airports