SYD - CHI

$736 Find Cheap Flights from Sydney to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 15/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago.
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Flight Deals

Cheap Flights from Sydney to Chicago (SYD-CHI)

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

Tue, 4 Nov - Sun, 16 Nov
Alaska Airlines Logo
21:40 - 23:59SYD-ORD
43h 19m2 stops
Alaska Airlines Logo
09:20 - 19:45ORD-SYD
41h 25m2 stops
$1,474Alaska Airlines
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Tue, 30 Sep - Wed, 12 Nov
Air New Zealand Logo
08:55 - 21:24SYD-ORD
27h 29m2 stops
Air New Zealand Logo
14:30 - 08:45ORD-SYD
25h 15m2 stops
$1,488Air New Zealand
Find Deal
Sun, 2 Nov - Tue, 18 Nov
Air New Zealand Logo
11:45 - 01:15SYD-ORD
29h 30m2 stops
Air New Zealand Logo
13:00 - 10:30ORD-SYD
28h 30m2 stops
$1,490Air New Zealand
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Fri, 10 Oct - Fri, 17 Oct
United Airlines Logo
10:30 - 17:05SYD-ORD
22h 35m2 stops
United Airlines Logo
16:40 - 07:55ORD-SYD
23h 15m2 stops
$1,618United Airlines
Find Deal
Wed, 19 Nov - Mon, 24 Nov
ANA Logo
12:25 - 07:20SYD-ORD
35h 55m1 stop
ANA Logo
18:00 - 20:15ORD-SYD
33h 15m2 stops
$1,639ANA
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Mon, 8 Sep - Mon, 15 Sep
American Airlines Logo
09:10 - 17:56SYD-ORD
23h 46m1 stop
American Airlines Logo
15:52 - 07:05ORD-SYD
24h 13m1 stop
$1,676American Airlines
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Tue, 30 Sep - Wed, 12 Nov
American Airlines Logo
09:10 - 18:08SYD-ORD
23h 58m2 stops
American Airlines Logo
13:49 - 09:00ORD-SYD
26h 11m1 stop
$1,678American Airlines
Find Deal
Mon, 22 Sep - Mon, 29 Sep
United Airlines Logo
10:20 - 17:08SYD-ORD
21h 48m1 stop
United Airlines Logo
16:40 - 07:00ORD-SYD
23h 20m1 stop
$1,758United Airlines
Find Deal
Mon, 3 Nov - Wed, 19 Nov
Air Canada Logo
08:30 - 14:41SYD-ORD
23h 11m2 stops
Air Canada Logo
08:00 - 09:35ORD-SYD
32h 35m2 stops
$1,820Air Canada
Find Deal
Sat, 1 Nov - Mon, 17 Nov
Air Canada Logo
10:20 - 19:30SYD-ORD
25h 10m2 stops
Air Canada Logo
08:00 - 09:35ORD-SYD
32h 35m2 stops
$1,846Air Canada
Find Deal
Booking Insights

KAYAK's insights & trends for Sydney to Chicago flights

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

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

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

For Sydney to Chicago, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Sydney, the best deals are generally found on Friday, with Thursday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Sydney to Chicago, 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 Sydney to Chicago is February, where tickets cost $1,142 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $2,428 and $1,987 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Sydney to Chicago, 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 Sydney to Chicago, you should book around 4 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$736
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Sydney to Chicago O'Hare Airport

When to book flights from Sydney to Chicago

Are your dates flexible? Find out the best times to travel from Sydney to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns 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 Sydney to Chicago

  • What is the cheapest flight from Sydney to Chicago?

    In the last 3 days, the lowest price for a flight from Sydney to Chicago was $478 for a one-way ticket and $957 for a return.

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

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

  • Which airline alliances offer flights from Sydney to Chicago?

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

  • Which is the best airline for flights from Sydney to Chicago, ANA or Air New Zealand?

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are ANA and Air New Zealand. With an average price for the route of $1,829 and an overall rating of 8.4, ANA is the most popular choice. Air New Zealand is also a great choice for the route, with an average price of $1,654 and an overall rating of 8.0.

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

    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 Sydney to Chicago.

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

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Sydney with another airline.

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

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

Reviews of the top 5 airlines flying from Sydney to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Sydney to Chicago. 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 Sydney to Chicago? 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 943 reviews
8.6Boarding
8.7Crew
8.2Comfort
7.7Food
7.9Entertainment
Airline reviews

One of the best business class seats I’ve had. The lie flat seats made it comfortable to endure a 12 hour flight. Service was excellent and food was great.

10.0 ExcellentAnthony, Aug 2025NRT - ORD
Read more ANA reviews

One of the best business class seats I’ve had. The lie flat seats made it comfortable to endure a 12 hour flight. Service was excellent and food was great.

Almost 6 hours of delay with over 12 gate changes. Flight was supposed to depart around 6 and instead depart after 12am. No accommodations were offered than some snacks closer to midnight when the crew was planning to throw away some snacks.

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

The crew was excellent. The flight was delayed for 20 to 25 minutes. We did arrive a bit later than expected. The AC could have been better.

Very disappointed with the seat selection. During the booking, I selected seats such that my wife and I would sit next to each other. However, during check-in, we found out that the airline changed our seats and we were seated apart; and I was stuck in the middle seat with two strangers. Very disappointing experience. We would not fly ANA next time.

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.

Upgrade the comfort, food and attendants. Also we arrived in Houston in the morning. The meal they served two hours before our arrival was a dinner entree. It would have been a lot nicer and much more appropriate to have had breakfast.

Every leg of the flight was late causing us to miss our flight to Okinawa and have to take the next flight out.

Wonderful I would recommend it to fly & ride with ANA.

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

Not a comfortable trip, the seats are not good, and they look old.

Lost my luggage and brought someone else luggage to my airport.

Not entirely positive. It’s frustrating that everything is done through the united app. One of our flight attendants on our trip from San Francisco to MSP continually had trouble hearing people so she flipped her hair into people’s faces

I flew United from San Francisco to Auckland. My connecting flight from Auckland to Christchurch was canceled with no explanation. I was finally told the cancellation was due to fog. Even though it was clear when we landed. I am from San Francisco, I know what fog is! And I didn't see any fog. I was told the next available flight was 7 hours later. Unacceptable, they should have had a flight ready to go as soon as it was deemed safe to take off.

Full flight. Flight attendants were harried. Otherwise, fine for the typical cramped seating conditions in coach.

Great! Flight was delayed by 30 mins but all was great. Thanks.

The 10hr flight was a comfortable as it could be in row 57. The food was just very bad….bland and soggy!

The business class upgrade meant a good sleep on the way home after a long week away. Excellent service, great food, and comfortable seat/bed for the journey.

I love the “boarding from the back” idea - it’s so much better than the “Zones” idea that many others use. Also, the inflight wifi was a first for me! Very nice to have on a 13-hour flight!

Again, Air New Zealand was great. They kept bathrooms clean, food was actually very good, New Zealand wines a big hit

My flight from Dallas to Sydney was cancelled. My entire trip was rerouted to include the following: Hartford to Washington DC Washington DC to JFK JFK to Auckland Auckland to Christchurch I paid for an aisle seat on the flight to Auckland and was asked if I would take a window seat to accommodate a family. The agent at the podium failed to mention that the family had a 3 month old baby and that a bassinet would be used during the 16 hour flight. The only way I could get out of my seat was to crawl under the bassinet of the sleeping baby. I think it is wrong that I was no given the choice to sit in another seat, that the agent knew what she was doing and chose to not properly disclose my seating arrangement. Terrible treatment.

they ran out of fruit for breakfast and so I just had a yogurt instead. other than that the flight was good

by the time they got to our row, they were out of some of the food options. games and movies were great but maybe more game options like tetris or pac man would be great

A few more inches of legroom is all i ask

Great as usual, some delays but well communicated and made up for in the air

Poor! This flight was delayed 14 hours. There was no assistance in helping customers find other routes to their destination, nor any other kind of support. It was a chaotic experience. I'm not likely to fly with AA going forward.

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.

We were upgraded and after just a short delay in attending to a safety check we were on our way. Would definately fly Qantas International on their Dreamliner again.

I tried to check in online but was unable to do so. I stood in line for nearly two hours to check in. American Airlines was understaffed. When I finally got to the kiosk to check in, I was still unable to check in. No AA staff was available to help. Finally one of the airport security agents who was helping passengers became of lack of AA Staff told me: “I think the reason you can’t check in is that you are starting your name with an upper case letter when you write it. Just write it with all lower case letters.” That did allow me to check in. HOW COULD ANYONE POSSIBLY KNOW THAT IF THEY USE AN INITIAL UPPER CASE LETTER TO SPELL THEIR OWN NAME, AA WOULD NOT ALLOW THEM TO CHECK IN?????? Then I had to wait in line over half an hour again to drop off my baggage. Although I arrived at the airport 3 hours early, by the time I got to the gate, they had already started boarding.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

I found the staff to not be very attentive at all. When paying for Business Class you expect a certain type of service and that was not found. They were almost rude even

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

Terrible, return flight was cancelled a night before the flight was scheduled to depart and I was notified by an email and an automated message on their phone line. I’ll never book Air Canada again

Could not understand what the attendant was saying during his announcements.

The flight attendants were not very nice. No smiles On my return trip I was charged for one bag $83.30 although I had purchased the flight including one piece of luggage. Can this be refunded to me? Thank you!

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

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

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