SYD - CHI

$869 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 14/4. 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.
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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Everything you should know

Cheapest return fare
$1,309
Typical prices: $1,058-$1,971
Multiple Airlines
Fri 17/4Fri 24/4
SYD - ORD • 2 stops
Cheapest one-way flight
$869
Typical prices: $673-$1,530
Multiple Airlines
Tue 14/4
SYD - ORD • 3 stops
Top airlines
American Airlines
Cheapest • from $1,579 (return)
ANA
Best reviews • 8.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct 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 stopover airports
San Francisco (SFO)
Cheapest • Avg $1,510 (return)
Dallas (DFW)
Shortest trip • 19h 51m (one-way)
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 19% 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 hundreds 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 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

Fri, 17 Apr - Fri, 24 Apr
Multiple Airlines Logo
06:00 - 23:27
SYD
-
ORD
32h 27m
2 stops
Multiple Airlines Logo
14:00 - 11:50
ORD
-
SYD
30h 50m
2 stops
$1,309Multiple Airlines
Thu, 16 Apr - Thu, 23 Apr
Multiple Airlines Logo
13:15 - 23:27
SYD
-
ORD
25h 12m
2 stops
Multiple Airlines Logo
14:00 - 11:50
ORD
-
SYD
30h 50m
2 stops
$1,446Multiple Airlines
Fri, 17 Apr - Fri, 24 Apr
Multiple Airlines Logo
13:15 - 05:35
SYD
-
ORD
31h 20m
2 stops
Multiple Airlines Logo
14:00 - 11:50
ORD
-
SYD
30h 50m
2 stops
$1,487Multiple Airlines
Wed, 6 May - Wed, 6 May
American Airlines Logo
09:10 - 18:05
SYD
-
ORD
23h 55m
2 stops
American Airlines Logo
20:49 - 07:05
ORD
-
SYD
43h 16m
2 stops
$1,579American Airlines
Mon, 13 Jul - Mon, 10 Aug
American Airlines Logo
09:10 - 16:41
SYD
-
ORD
22h 31m
1 stop
American Airlines Logo
18:03 - 07:05
ORD
-
SYD
22h 02m
1 stop
$1,604American Airlines
Mon, 13 Jul - Mon, 10 Aug
American Airlines Logo
09:10 - 14:18
SYD
-
ORD
20h 08m
1 stop
American Airlines Logo
15:12 - 07:05
ORD
-
SYD
24h 53m
1 stop
$1,611American Airlines
Mon, 13 Jul - Mon, 10 Aug
American Airlines Logo
06:25 - 15:48
SYD
-
ORD
24h 23m
2 stops
American Airlines Logo
15:52 - 07:05
ORD
-
SYD
24h 13m
2 stops
$1,643American Airlines
Thu, 16 Apr - Thu, 23 Apr
Delta Logo
09:15 - 17:58
SYD
-
MDW
23h 43m
2 stops
Delta Logo
13:24 - 06:50
MDW
-
SYD
26h 26m
2 stops
$1,788Delta
Thu, 26 Mar - Sun, 5 Apr
Delta Logo
09:40 - 18:40
SYD
-
MDW
25h 00m
2 stops
Delta Logo
14:05 - 06:50
MDW
-
SYD
25h 45m
2 stops
$1,789Delta
Fri, 10 Jul - Tue, 18 Aug
Delta Logo
09:15 - 18:05
SYD
-
MDW
23h 50m
2 stops
Delta Logo
14:00 - 06:50
MDW
-
SYD
25h 50m
2 stops
$1,803Delta
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 April, where tickets cost $1,204 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $1,896 and $1,643 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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$869
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 11% 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 $869 for a one-way ticket and $1,296 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, 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, 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 $1,880 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 $1,504 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 1108 reviews
7.7Food
8.5Boarding
7.9Entertainment
8.2Comfort
8.7Crew
Airline reviews

The food was not great and the seats you need a little bit more space to put your things down around you: the blankets and toiletry bag were good. Flight was on time and bags etc no issues

8.0 ExcellentJennifer, Feb 2026
HND - EWR
Read more ANA reviews

The food was not great and the seats you need a little bit more space to put your things down around you: the blankets and toiletry bag were good. Flight was on time and bags etc no issues

Entertainment was good , comfort on airplane easy hoarding food and drinks was good and a friendly and good service of flight staff

The plane was very clean and the crew was very nice.

The lounge in Japan was busy and smaller. Have great choice of ramen.

Customer service was very good. Food was delicious. Wish the flight was longer.

I was good seat to keep stretch my legs . but couldn’t keep my bag in my hand . because they told me can’t keep my seat is no holder , because no seat fronts of us. wish I can put my leg on something higher. but instead of that everything goood.

Overall was a good experience. Crew members are nice and helpful.

Good airlines btu ORL airport messed up the return flight for me. Checking out a connecting flight pax is unacceptable.

The pilot was kept warning about the weather terrifying us. The flight attendants were not warm or pleasant.

I couldn’t sit with my daughter. we are separate and both seat was not window or halway side. in the middle. if we sit together will be share comfort seat and more easy travel. this is bad.

This flight was the second leg of a trip that began in Auckland, New Zealand. I was unable to find a way to select seats in advance. The boarding passes we were given in Auckland did not have seat assignments for the second flight. There was no way to check on it until personnel showed up at the gate in Los Angeles, immediately before boarding time. The flight was overbooked by one, and since I was traveling with my sister, we needed two seats. We waited in considerable anxiety for everyone else to board and when one person did not show up, we had to take whatever was left. At least we finally got on the flight although we were the very last to board. We were not able to sit together, of course.

The Premium Economy seats were very comfortable and the food was quite tasty. I did not use the entertainment system, but I was able to charge my phone and tablet with the seatback connection.

The seats are feeling very hard to sit on. All the padding is flat, like sitting on a park bench for over an hour

We had difficulty checking in as United didn’t recognize the confirmation number and the agent was not helpful. We went to the United Assistance desk where the agent was able to process our reservation. We also weren’t allowed to choose seats in advance.

Your entertainment could be better. I flew on Air New Zealand in January so was expecting a better choice in February...but no luck. Same choices and also could have a better selection. Otherwise, lovely service, the purser came to our seats to welcome us. Overall, very nice. Direct flight from Auckland to YVR was fantastic!

Air New Zealand over sold our flight and tried to bump us to yesterday. After several calls we got booked to United about 6 hrs before our original flight. No apologies!

Very quick flight so no time for refreshments. We took off. Then landed. The end. Seats were too tight. Very cramped Grateful for the short flight cos moving around wasn’t possible

Please add more Bollywood movies and recent movies to the entertainment.

I was not even on that flight and did not even book a ticket. Kayak did a phenomenal job

Entertainment screen froze and had to be reset. Noticed it happened to other passengers as well.

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.

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

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.

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.

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

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.

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

Other airlines flying from Sydney to Chicago

Flights from the other most popular airlines that fly from Sydney to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.