SYD - CHI

$425 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 10/15. 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

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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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

Sat, Nov 8 - Sat, Nov 22
Air Canada Logo
11:20 am - 3:10 pmSYD-ORD
44h 50m2 stops
Air Canada Logo
3:40 pm - 9:35 amORD-SYD
24h 55m1 stop
$868Air Canada
Find Deal
Mon, Oct 6 - Thu, Dec 25
Air Canada Logo
10:20 am - 3:00 pmSYD-ORD
20h 40m1 stop
Air Canada Logo
8:00 am - 6:55 amORD-SYD
29h 55m2 stops
$871Air Canada
Find Deal
Tue, Sep 30 - Wed, Nov 12
Qantas Airways Logo
9:10 am - 3:51 pmSYD-ORD
21h 41m1 stop
Qantas Airways Logo
6:03 pm - 9:00 amORD-SYD
21h 57m1 stop
$947Qantas Airways
Find Deal
Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
10:10 am - 1:38 pmSYD-MDW
43h 28m2 stops
Multiple Airlines Logo
5:10 am - 8:05 amMDW-SYD
34h 55m2 stops
$954Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
11:20 am - 12:37 pmSYD-MDW
41h 17m2 stops
Multiple Airlines Logo
6:25 am - 7:25 amMDW-SYD
32h 00m2 stops
$966Multiple Airlines
Find Deal
Tue, Sep 30 - Wed, Nov 12
American Airlines Logo
9:10 am - 5:18 pmSYD-ORD
23h 08m2 stops
American Airlines Logo
3:00 pm - 9:00 amORD-SYD
25h 00m1 stop
$987American Airlines
Find Deal
Tue, Sep 30 - Wed, Nov 12
Delta Logo
9:25 am - 6:35 pmSYD-MDW
24h 10m2 stops
Delta Logo
1:14 pm - 8:30 amMDW-SYD
26h 16m2 stops
$1,004Delta
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Tue, Sep 30 - Wed, Nov 12
Delta Logo
9:25 am - 7:00 pmSYD-ORD
24h 35m2 stops
Delta Logo
1:38 pm - 8:30 amORD-SYD
25h 52m2 stops
$1,004Delta
Find Deal
Sat, Oct 4 - Tue, Dec 23
American Airlines Logo
9:10 am - 9:22 pmSYD-ORD
27h 12m1 stop
American Airlines Logo
12:15 pm - 6:10 amORD-SYD
24h 55m1 stop
$1,053American Airlines
Find Deal
Wed, Nov 26 - Tue, Jan 27
Qantas Airways Logo
5:45 pm - 11:59 pmSYD-ORD
23h 14m1 stop
Qantas Airways Logo
12:25 pm - 6:10 amORD-SYD
24h 45m1 stop
$1,057Qantas Airways
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $868 (round-trip)
Qantas Airways
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 21% 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
Cheapest round-trip
$868
Overall average: $1,126
Air Canada
Sat 11/8Sat 11/22
SYD - ORD • 2 stops
Cheapest one-way
$425
Typical prices: $553-947
Multiple Airlines
Wed 10/15
SYD - ORD • 2 stops
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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!
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.

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

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 $741 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $1,531 and $1,275 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 2 weeks before departure, which saves you about 21% 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$425
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 8% 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 $425 for a one-way ticket and $868 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?

    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, 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 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.
7.5
Qantas AirwaysOverall score based on 907 reviews
7.2Entertainment
7.7Boarding
7.5Comfort
8.2Crew
7.0Food
Airline reviews

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.

2.0 MediocreAnonymous, Aug 2025BDL - DFW
Read more Qantas Airways reviews

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.

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.

One of the oldest most uncomfortable "lay down" seats I've ever experienced. Old plane and old seats that don't lay flat. The seat back does not even recline - at all. Instead the legrest awkwardly extends to fill the gap between a small cubby into which you must insert your feet/legs. I am 5' 11" and could not lay straight but had to tuck my knees. Ticket was also very expensive. Would not recommend flying business/first on Finair from Melbourne to Bangkok and will not do so again myself.

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

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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

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