SYD - CHI

$493 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 3/8. 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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Everything you should know

Cheapest round-trip
$1,051
Typical prices: $705-$963
Air Canada
Tue 2/17Wed 3/4
SYD - ORD • 1 stop
Cheapest one-way
$535
Typical prices: $473-$943
Multiple Airlines
Sun 3/8
SYD - ORD • 3 stops
Top airlines
Air New Zealand
Cheapest • from $1,038 (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 24% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 24% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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, Feb 17 - Wed, Mar 4
Air Canada Logo
11:20 am - 2:41 pm
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
3:35 pm - 9:35 am
ORD
-
SYD
25h 00m
1 stop
$1,051Air Canada
Tue, Feb 17 - Wed, Mar 4
Air Canada Logo
11:20 am - 8:10 pm
SYD
-
ORD
25h 50m
2 stops
Air Canada Logo
3:35 pm - 9:35 am
ORD
-
SYD
25h 00m
1 stop
$1,054Air Canada
Tue, Feb 17 - Wed, Mar 4
Air Canada Logo
11:20 am - 8:10 pm
SYD
-
ORD
25h 50m
2 stops
Air Canada Logo
12:50 pm - 9:35 am
ORD
-
SYD
27h 45m
2 stops
$1,058Air Canada
Thu, Feb 26 - Thu, Mar 5
Air Canada Logo
11:20 am - 4:45 pm
SYD
-
ORD
46h 25m
2 stops
Air Canada Logo
3:35 pm - 9:35 am
ORD
-
SYD
25h 00m
1 stop
$1,062Air Canada
Wed, Feb 18 - Thu, Mar 5
Air Canada Logo
11:20 am - 10:04 pm
SYD
-
ORD
27h 44m
2 stops
Air Canada Logo
3:35 pm - 9:35 am
ORD
-
SYD
25h 00m
1 stop
$1,068Air Canada
Wed, Feb 18 - Thu, Mar 5
Air Canada Logo
11:20 am - 2:41 pm
SYD
-
ORD
20h 21m
1 stop
Air Canada Logo
3:35 pm - 9:35 am
ORD
-
SYD
25h 00m
1 stop
$1,070Air Canada
Mon, Apr 13 - Wed, Apr 22
Delta Logo
9:15 am - 5:58 pm
SYD
-
MDW
23h 43m
2 stops
Delta Logo
10:43 am - 6:50 am
MDW
-
SYD
29h 07m
2 stops
$1,448Delta
Fri, Jun 26 - Wed, Jul 15
Delta Logo
9:15 am - 8:38 am
SYD
-
MDW
38h 23m
2 stops
Delta Logo
1:00 pm - 6:50 am
MDW
-
SYD
26h 50m
2 stops
$1,484Delta
Sun, Jun 28 - Sat, Jul 18
Delta Logo
9:15 am - 6:05 pm
SYD
-
MDW
47h 50m
2 stops
Delta Logo
6:45 pm - 6:50 am
MDW
-
SYD
45h 05m
2 stops
$1,588Delta
Sat, Mar 14 - Sat, Mar 21
Multiple Airlines Logo
2:00 pm - 8:21 pm
SYD
-
MDW
22h 21m
2 stops
Multiple Airlines Logo
9:16 pm - 6:55 am
MDW
-
SYD
41h 39m
1 stop
$1,597Multiple Airlines
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 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 November, where the average cost of round-trip tickets is $1,337 and $1,155 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 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$535
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 12% 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 $493 for a one-way ticket and $1,038 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 $982 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 $1,587 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 981 reviews
7.0Food
7.7Boarding
7.5Comfort
7.2Entertainment
8.2Crew
Airline reviews

Hard to move and get out of my seat when the passenger in front is in recline position.

2.0 MediocreAnonymous, Jan 2026
MEL - LAX
Read more Qantas Airways reviews

Hard to move and get out of my seat when the passenger in front is in recline position.

It was a good flight and no complaints. It just wasn't anything that was better than any other flight.

The crew were wonderful - if only the customers were as well behaved as the attendants!! Ha ha! If you could just talk to God and ask for less turbulence next time.... Juuuuust kidding....

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.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

It was good but only meal served is very less. Meantime good to add rice and chicken in one of meal

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

Better entertainment & food options more may be adding chicken option or on vegetarian side good quality pasta

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

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.

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

Information on your arrival and departure airports