CHI - SYD

$459 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 5/9. 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
$971
Typical prices: $1,447-$1,204
Multiple Airlines
Tue 4/21Tue 4/28
ORD - SYD • 2 stops
Cheapest one-way
$459
Typical prices: $634-$849
Multiple Airlines
Sat 5/9
ORD - SYD • 2 stops
Top airlines
Cheapest • from $1,145 (round-trip)
Best reviews • 8.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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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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Top layover airports
Cheapest • Avg $785 (round-trip)
Shortest trip • 18h 53m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 18% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
Good to know
+1
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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

Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
7:30 am - 11:50 am
ORD
-
SYD
37h 20m
2 stops
Multiple Airlines Logo
1:15 pm - 11:27 pm
SYD
-
ORD
25h 12m
2 stops
$971Multiple Airlines
Wed, May 20 - Wed, Jun 3
Multiple Airlines Logo
7:30 am - 11:50 am
ORD
-
SYD
37h 20m
2 stops
Multiple Airlines Logo
1:20 pm - 5:35 am
SYD
-
ORD
31h 15m
2 stops
$983Multiple Airlines
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
6:55 am - 11:50 am
ORD
-
SYD
37h 55m
3 stops
Multiple Airlines Logo
6:00 am - 11:13 pm
SYD
-
ORD
56h 13m
3 stops
$1,007Multiple Airlines
Mon, May 11 - Mon, Jun 1
Multiple Airlines Logo
2:39 pm - 12:05 pm
ORD
-
SYD
30h 26m
2 stops
Multiple Airlines Logo
1:15 pm - 11:27 pm
SYD
-
ORD
25h 12m
2 stops
$1,040Multiple Airlines
Thu, Apr 23 - Sun, May 3
Multiple Airlines Logo
2:00 pm - 11:50 am
ORD
-
SYD
30h 50m
2 stops
Multiple Airlines Logo
1:15 pm - 5:35 am
SYD
-
ORD
31h 20m
2 stops
$1,071Multiple Airlines
Sun, May 24 - Wed, Jun 3
Air Canada Logo
3:40 pm - 7:20 am
ORD
-
SYD
24h 40m
1 stop
Air Canada Logo
9:20 am - 2:45 pm
SYD
-
ORD
20h 25m
1 stop
$1,145Air Canada
Fri, May 15 - Sat, May 23
Air Canada Logo
3:40 pm - 7:20 am
ORD
-
SYD
24h 40m
1 stop
Air Canada Logo
9:20 am - 2:45 pm
SYD
-
ORD
20h 25m
1 stop
$1,146Air Canada
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:16 pm - 6:50 am
MDW
-
SYD
26h 34m
2 stops
Delta Logo
9:15 am - 6:05 pm
SYD
-
MDW
23h 50m
2 stops
$1,611Delta
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:49 pm - 6:50 am
MDW
-
SYD
26h 01m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,612Delta
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:49 pm - 6:50 am
MDW
-
SYD
26h 01m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
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 April.

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 February, where tickets cost $1,149 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $1,544 and $1,535 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 2 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$459
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 10% 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 3 days, the lowest price for a flight from Chicago to Sydney was $459 for a one-way ticket and $971 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 $1,246 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 $1,155 and an overall rating of 8.1.

  • 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 1157 reviews
8.2Comfort
8.7Crew
8.0Entertainment
7.8Food
8.5Boarding
Airline reviews

Suite lounge in Honolulu is the best lounge in Honolulu. I love the huge bathrooms in ANA first Class on the A380 Honu plane. Japanese meal was outstanding and service was amazing. Everything was just excellent. Can’t wait to fly again

10.0 Excellentmichael, Mar 2026
HNL - NRT
Read more ANA reviews

Suite lounge in Honolulu is the best lounge in Honolulu. I love the huge bathrooms in ANA first Class on the A380 Honu plane. Japanese meal was outstanding and service was amazing. Everything was just excellent. Can’t wait to fly again

Their was $200 charge for 2nd luggage, airplane very new and flight smooth. Flight time seem faster then Asian stoping Korea then china.

Flight was late boarding. United crew were not friendly and cordial unlike the ANA crew.

Seat was broken. Check in was not possible until we reached the gate, by then we were separated.

The food was not great; but I don’t expect much from airline food. However, the staff was incredible! I had gotten to the gate when I realized I had left my computer at the security checkpoint! I told a staff member and she said, “well, you will miss this flight if you go back to get it” It was a long way from the gate. I asked if I might get on the next flight. She sent for another staff member, and he took me to the gate desk. He found an open seat, and said,”okay, go run to get your computer, I will get you a new boarding pass.” I rran back, retrieved my computer, and returned to the gate. It was closed, but I found the gate nearby where the next ANA flight was leaving. Another staff member was ready for me, and printed me a new pass, and even made sure I still had an aisle seat that I requested! I got in line and continued my trip. These people are amazing, helpful, and friendly. My trip could have been ruined, or postponed at a great expense, but they saved the day! 5 stars!!!!

I originally thought I was booking with ANA airlines and didn't see "operated by United" until the day of. I even thought the United check-in update was a scam so ended up checking in 3 hours before the flight, causing separate seating and uncomfortable middle seats.

Very disappointing. Our flight was delayed for almost 6 hours with the lost time disrupting our travel plans. United should have known that any delay (approximately and hour) triggered a no-fly/work because according to the FAA they had to many flight hours. After the mechanical delay (approximately an hour) we had to wait for a fresh crew change. Seems to me that United could have anticipated this incident. Again, a very disappointing travel experience.

Excellent crew, food and comfort from LA to Narita. Flight from Narita to Manila was just okay, Food and comfort needs to improve. The business class was not comfortable.

Plane and boarding was on time. It was easy to check in online and then just drop off bags. Will fly with then again.

Lots of leg room in premium. Departed exactly on time. Friendly crew.

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

This was the worst flight I’ve been on. Getting on the plane where is was 30 degrees outside was hotter on board cabin must’ve been 33 degrees. This is a health hazard. They cannot be doing this to save on fuel. People could die from this!!. Fans and a/c was, off entertainment was off. Poor excuse given. Crew made the excuse that the system didn’t have enough power. They basically were operating on one engine to save on jet fuel till 3 hours later on cruising altitude and they then started the second engine. And finally the cabin was cooled. On a 7hour red eye flight this made it so uncomfortable and impossible to sleep.

My experience was great overall. Tanya was particularly friendly and helpful the entire trip. I was very pleased with her customer service skills. The plane was an older aircraft but the entire way was comfortable with barely any turbulence at all. Qantas should speed up its fleet renovation. Totally recommend using this airline.

Qantas is always subpar beyond comfy chairs for a domestic flight

I liked boarding the plane. The staff were rude, the food was appalling and the chairs the most uncomfortable I have ever experienced

an hour late, then had to disembark on back stairs and take 4 flights up to get to main airport. No warning, and difficulty for those with canes and poor knees.

Well my expórtenle with Qantas it wasn’t that good KLM from Bs Aires was delay Santiago Chile Qantas QF 028 was still in the airport but the crew didn’t opened the door for me soo I lost my fly And I stuck in the airport 13 hrs waiting for next fly by Latam Arline My question is can I have my money back for business class

It was ok, the additional baggage charges were a bit excessive given winter is a time for skiing. To have to pay $600 extra for skis was tantamount to robbery. Airlines should consider sporting goods as baggage. Likewise, they should consider increasing the number of bags allowed on international flights to known ski destinations.

Flight was canceled. I was not alerted. It was only kayak that alerted me

Flight was 2.5 hours late leaving. We spent 50 minutes of that sitting on the plane with no explanation. They did reduce the time in the air so we arrived a little less late which was something. The cheese and crackers were okay but the wine was terrible.

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

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.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Very rude gate attendants in San Francisco who didn’t let me bring my little carry on (smaller than usual size) and after boarding I realized that there still were a lot of overhead compartment space (like a full section available in some spots). That made me lose 30 minutes at my destination at 1am and it could have broken something fragile that I had in it

The most uncomfortable flight I’ve ever been on. I’m only 5,4” and barely had enough room to exist, couldn’t even fully relax my shoulders. Not sure why they bother with snacks. Half a coke and a single cookie?? Wow. Purchasable food looked gross too. Remember when airlines used to treat you like a human being?

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.

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

Information on your arrival and departure airports