SYD - CHI

$619 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 5/17. 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
$902
Typical prices: $1,003-$1,553
Air Canada
Mon 4/20Thu 4/30
SYD - ORD • 2 stops
Cheapest one-way
$619
Typical prices: $710-$1,095
Air New Zealand
Sun 5/17
SYD - ORD • 2 stops
Top airlines
Cheapest • from $902 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Sydney and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $1,010 (round-trip)
Shortest trip • 19h 36m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 17% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 10% price drop
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

Mon, Apr 20 - Thu, Apr 30
Air Canada Logo
9:20 am - 4:35 pm
SYD
-
ORD
22h 15m
2 stops
Air Canada Logo
3:40 pm - 7:20 am
ORD
-
SYD
24h 40m
1 stop
$902Air Canada
Mon, Apr 20 - Thu, Apr 30
Air Canada Logo
9:20 am - 8:05 pm
SYD
-
ORD
25h 45m
2 stops
Air Canada Logo
9:50 am - 7:20 am
ORD
-
SYD
30h 30m
2 stops
$906Air Canada
Thu, Apr 30 - Thu, May 7
Air Canada Logo
9:20 am - 8:08 pm
SYD
-
ORD
49h 48m
2 stops
Air Canada Logo
3:40 pm - 7:20 am
ORD
-
SYD
24h 40m
1 stop
$930Air Canada
Fri, May 1 - Fri, May 8
Multiple Airlines Logo
1:15 pm - 5:35 am
SYD
-
ORD
31h 20m
2 stops
Multiple Airlines Logo
5:15 am - 10:10 pm
ORD
-
SYD
49h 55m
2 stops
$934Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Air Canada Logo
9:20 am - 8:00 am
SYD
-
ORD
37h 40m
2 stops
Air Canada Logo
9:20 pm - 7:20 am
ORD
-
SYD
43h 00m
2 stops
$945Air Canada
Thu, Apr 30 - Thu, May 7
Air Canada Logo
9:20 am - 8:15 pm
SYD
-
ORD
25h 55m
1 stop
Air Canada Logo
3:40 pm - 7:20 am
ORD
-
SYD
24h 40m
1 stop
$948Air Canada
Wed, Apr 22 - Sun, Apr 26
Air Canada Logo
9:20 am - 2:45 pm
SYD
-
ORD
20h 25m
1 stop
Air Canada Logo
9:20 pm - 7:20 am
ORD
-
SYD
43h 00m
2 stops
$964Air Canada
Wed, Apr 29 - Wed, May 6
Delta Logo
9:15 am - 5:58 pm
SYD
-
MDW
23h 43m
2 stops
Delta Logo
12:52 pm - 6:50 am
MDW
-
SYD
26h 58m
2 stops
$1,503Delta
Tue, Apr 28 - Tue, May 5
Delta Logo
9:15 am - 5:58 pm
SYD
-
MDW
23h 43m
2 stops
Delta Logo
1:24 pm - 6:50 am
MDW
-
SYD
26h 26m
2 stops
$1,514Delta
Tue, Jul 14 - Tue, Sep 15
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
Delta Logo
2:00 pm - 6:50 am
MDW
-
SYD
25h 50m
2 stops
$1,525Delta
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Sydney to Chicago departing in April.

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 August, where tickets cost $1,047 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $1,331 and $1,276 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 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$619
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 6% 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 $619 for a one-way ticket and $902 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, and oneworld 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 $1,181 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 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 1005 reviews
7.4Comfort
7.2Entertainment
7.0Food
7.7Boarding
8.1Crew
Airline reviews

We booked with Qantas instead of Delta and we instead flew on American Airlines. American is not our favorite to go on. No leg room and the width of seats are a joke. Your are packed like sardines on American flights.

6.0 GoodLarry, Mar 2026
AKL - LAX
Read more Qantas Airways reviews

We booked with Qantas instead of Delta and we instead flew on American Airlines. American is not our favorite to go on. No leg room and the width of seats are a joke. Your are packed like sardines on American flights.

When I originally booked this flight, I was expecting to travel on Qantas. When the itinerary changed and the long-haul segment was operated by American Airlines, we were disappointed but remained open-minded. Unfortunately, the overall service experience fell far short of expectations. This was a long-haul international flight. Getting up periodically to use the restroom or stretch is inevitable, especially on flights of this duration. However, each time we stood up, we felt as though we were inconveniencing the crew. The tone and body language often suggested that we were in the way or disrupting something simply by moving about the cabin. As a result, I avoided getting up as often as I needed to and was physically very sore upon arrival. Meal service was similarly impersonal. The options were presented in single words “beef or veggie,” “pasta or beef” without any description of what was actually being served. There was little engagement or courtesy beyond that. Even simple expressions of gratitude were often not acknowledged. I am accustomed to no-frills travel and do not expect luxury. What was disappointing was not the absence of extras, but the absence of basic warmth and professionalism. On a long-haul international flight, small moments of courtesy and humanity make a significant difference. In this case, the experience felt transactional and dismissive rather than welcoming. I hope this feedback is taken constructively, as there is a meaningful difference between efficient service and indifferent service.

Flight arrived late with no one to help over 30 people rebook. I slept at the airport.

Business seats not as comfortable or private as most competitors (e.g. Qantas was outstanding), and movie selection was much more limited than Qantas or United has been recently

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.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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.

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

Information on your arrival and departure airports