SYD - CHI

$589 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 11/15. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$938
Overall average: $1,126
Air New Zealand
Tue 11/18Wed 12/3
SYD - ORD • 2 stops
Cheapest one-way
$589
Typical prices: $950-$1,023
Air New Zealand
Sat 11/15
SYD - ORD • 2 stops
Top airlines
Air New Zealand
Cheapest • from $938 (round-trip)
Qantas Airways
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 27% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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 round-trip 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 round-trip flight deals from Sydney to Chicago

Tue, Nov 18 - Wed, Dec 3
Air New Zealand Logo
9:55 am - 7:30 pmSYD-ORD
26h 35m2 stops
Air New Zealand Logo
10:38 am - 10:30 amORD-SYD
30h 52m2 stops
$938Air New Zealand
Find Deal
Mon, Nov 17 - Mon, Dec 1
American Airlines Logo
11:20 am - 3:55 pmSYD-ORD
21h 35m1 stop
American Airlines Logo
1:49 pm - 9:00 amORD-SYD
26h 11m1 stop
$982American Airlines
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Sun, Mar 29 - Sat, Apr 11
United Airlines Logo
11:20 am - 6:08 amSYD-ORD
34h 48m1 stop
United Airlines Logo
9:21 pm - 6:55 amORD-SYD
42h 34m1 stop
$1,042United Airlines
Find Deal
Tue, Nov 18 - Wed, Dec 3
Qantas Airways Logo
11:20 am - 3:55 pmSYD-ORD
21h 35m1 stop
Qantas Airways Logo
11:45 am - 9:00 amORD-SYD
28h 15m1 stop
$1,048Qantas Airways
Find Deal
Sat, Jan 17 - Thu, Jan 22
Qantas Airways Logo
5:45 pm - 9:23 pmSYD-ORD
20h 38m1 stop
Qantas Airways Logo
11:56 am - 6:55 amORD-SYD
25h 59m1 stop
$1,076Qantas Airways
Find Deal
Sun, Mar 29 - Sat, Apr 11
Air Canada Logo
10:20 am - 4:36 pmSYD-ORD
46h 16m2 stops
Air Canada Logo
3:45 pm - 7:20 amORD-SYD
48h 35m2 stops
$1,110Air Canada
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Sat, Jan 17 - Thu, Jan 22
Air Canada Logo
11:20 am - 5:03 pmSYD-ORD
22h 43m2 stops
Air Canada Logo
1:13 pm - 9:35 amORD-SYD
27h 22m2 stops
$1,123Air Canada
Find Deal
Tue, Nov 18 - Wed, Dec 3
ANA Logo
9:45 pm - 5:16 amSYD-ORD
48h 31m2 stops
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
$1,167ANA
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Thu, Dec 25 - Sat, Jan 24
United Airlines Logo
11:20 am - 2:32 pmSYD-ORD
20h 12m1 stop
United Airlines Logo
7:58 pm - 6:20 amORD-SYD
41h 22m1 stop
$1,189United Airlines
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Fri, Jan 23 - Sun, Feb 22
ANA Logo
12:25 pm - 5:15 amSYD-ORD
33h 50m2 stops
ANA Logo
4:25 pm - 8:15 pmORD-SYD
34h 50m1 stop
$1,217ANA
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.

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Sydney to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Thursdays for the best deals.

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 March, where tickets cost $735 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $1,509 and $1,192 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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$589
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 7% 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 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 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 $589 for a one-way ticket and $938 for a round-trip.

  • Do I need a passport to fly between Sydney and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Sydney and on arrival in Chicago.

  • 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?

    oneworld is the only airline alliance operating flights between Sydney and Chicago.

  • Which is the best airline for flights from Sydney to Chicago, Qantas Airways or United Airlines?

    The two airlines most popular with KAYAK users for flights from Sydney to Chicago are Qantas Airways and United Airlines. With an average price for the route of $762 and an overall rating of 7.5, Qantas Airways is the most popular choice. United Airlines is also a great choice for the route, with an average price of $1,612 and an overall rating of 7.4.

  • 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 round-trip 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 3 airlines serving 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.
7.5
Qantas AirwaysOverall score based on 925 reviews
8.2Crew
7.5Comfort
7.0Food
7.2Entertainment
7.7Boarding
Airline reviews

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

6.0 GoodSandipan, Oct 2025SYD - DFW
Read more Qantas Airways reviews

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

No internet on flight, which makes log travels really hard.

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

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.

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

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

Information on your arrival and departure airports

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