SYD - CHI

$690 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 3/9. 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
$1,511
Typical prices: $2,308-$1,600
Multiple Airlines
Fri 1/5Sat 16/5
SYD - ORD • 2 stops
Cheapest one-way flight
$690
Typical prices: $1,260-$1,437
Multiple Airlines
Thu 3/9
SYD - ORD • 3 stops
Top airlines
Cheapest • from $1,662 (return)
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
Cheapest • Avg $1,508 (return)
Shortest trip • 19h 51m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 13% 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 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, 1 May - Sat, 16 May
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
06:55 - 22:10
ORD
-
SYD
48h 15m
3 stops
$1,511Multiple Airlines
Wed, 29 Apr - Tue, 5 May
Multiple Airlines Logo
13:15 - 06:08
SYD
-
ORD
31h 53m
3 stops
Multiple Airlines Logo
12:40 - 11:50
ORD
-
SYD
32h 10m
3 stops
$1,516Multiple Airlines
Tue, 28 Apr - Mon, 4 May
Multiple Airlines Logo
13:15 - 23:27
SYD
-
ORD
25h 12m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
2 stops
$1,536Multiple Airlines
Wed, 29 Apr - Tue, 5 May
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
12:40 - 22:10
ORD
-
SYD
42h 30m
3 stops
$1,538Multiple Airlines
Fri, 1 May - Sat, 16 May
Multiple Airlines Logo
13:15 - 05:50
SYD
-
ORD
31h 35m
2 stops
Multiple Airlines Logo
06:55 - 22:10
ORD
-
SYD
48h 15m
3 stops
$1,553Multiple Airlines
Wed, 27 May - Wed, 3 Jun
Multiple Airlines Logo
13:15 - 20:32
SYD
-
ORD
46h 17m
3 stops
Multiple Airlines Logo
06:55 - 11:50
ORD
-
SYD
37h 55m
3 stops
$1,559Multiple Airlines
Sun, 24 May - Sun, 31 May
Multiple Airlines Logo
13:15 - 05:59
SYD
-
ORD
31h 44m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
2 stops
$1,579Multiple Airlines
Fri, 1 May - Sat, 16 May
Multiple Airlines Logo
13:15 - 16:13
SYD
-
MDW
41h 58m
3 stops
Multiple Airlines Logo
06:00 - 22:10
MDW
-
SYD
49h 10m
3 stops
$1,591Multiple Airlines
Mon, 25 May - Mon, 1 Jun
Delta Logo
09:15 - 17:56
SYD
-
MDW
23h 41m
2 stops
Delta Logo
12:53 - 06:50
MDW
-
SYD
26h 57m
2 stops
$2,371Delta
Tue, 26 May - Tue, 2 Jun
Delta Logo
09:15 - 18:33
SYD
-
MDW
24h 18m
2 stops
Delta Logo
12:53 - 06:50
MDW
-
SYD
26h 57m
2 stops
$2,377Delta
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 return flight from Sydney to Chicago?

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

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 $1,487 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is $2,254 and $1,889 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 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$690
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly (5% more expensive 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 $690 for a one-way ticket and $1,511 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Sydney and Chicago, with oneworld 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 $1,877 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 $1,502 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 1171 reviews
7.8Food
8.6Boarding
8.2Comfort
8.7Crew
8.0Entertainment
Airline reviews

The seats were broken for several of us on this flight not to mention dirty. Quite unacceptable for the price point and expectation level. The meat was so hard it could hardly be cut so terribly unappealing. The united lungs in SFO was dirty and the bathroom conditions were down right disgusting. Nothing about this experience makes me want to book with United again. Our experiences with business class on Lufthansa and British Airways far out perform United in comparison. Truly disappointing!

2.0 MediocreAnonymous, Apr 2026
NRT - SFO
Read more ANA reviews

The seats were broken for several of us on this flight not to mention dirty. Quite unacceptable for the price point and expectation level. The meat was so hard it could hardly be cut so terribly unappealing. The united lungs in SFO was dirty and the bathroom conditions were down right disgusting. Nothing about this experience makes me want to book with United again. Our experiences with business class on Lufthansa and British Airways far out perform United in comparison. Truly disappointing!

It was good. The crew was efficient, food was good

They did not get back tickets in time about flight varification so i had to purchase another one way ticket to get home soxas rocnot Risk being unable to return home.

Food looked great but did not taste all that good.

Everything about the flight was good or very good. The only bummer was that there was a 2 hour delay and that's not the fault of the airlines but it still takes away from the whole experience. The most amazing thing was that our bags got to baggage claim in record time! That was excellent!

Flight was late boarding. United crew were not friendly and cordial unlike the ANA crew.

Vegetarian options were not that great. However, the crew and service was awesome

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.

Time to upgrade those planes so you can provide first class.

My experience with Underpricer was not great. The representative assigned to me did not tell me beforehand that selecting seats, which i could not do through ANZ, WOULD ADD SIGNIFICANT cost to my ticket (all flight segments were reg economy seats. The seat selections for the ticket, MCI-AKL, AKL-PER, PER-MCI, cost $284 USD. I WAS NOT TOLD AHEAD OF SELECTING SEATS chosen by the rep OF THE COSTS and never received an itemized invoice of the seat selections.). The costs of seat selection, an option solicited as a service, with no mention of costs, should have been disclosed to me prior to seat selection and certaily should have been itemized. For all I know, the $284 was not referred from the airline but made up and taken directly by Underpricer. Next, when i checked in, united couldnt find my ticket. This is probably why i didnt get a seat selection on that flight and couldnt check in online, despite Underpricer prompts to do so a week before departure, or at the kiosk at the airport. I had to wait for special help at the counter, then was told that because the flight segment, MCI-IAH, operated by United Airlines via the ANZ. ticket, had changed schedule slightly since I BOOKED MY FLIGHT, the MCI-IAH segment had been decoupled from the rest of the ticket because the IAH layover was now 12.5 hrs AND DID NOT QUALIFY AS A THROUGH FLIGHT TO AKL.. This meant my checked bag could not be checked through to AKL and id have to pick it up at IAH, THEN WAIT MOST OF the long layover WITH the large checked bag until ANZ counter in IAH OPENED for checkING just prior to the flight. Apparently, although underpricer had notified me of schedule changes, they did not update the ANZ TICKET, leading to this problem. Finallly, although I RECHECKED TH BAG IN At IAH 3.5-4 hours before the scheduled departure and the IAH-AKL segment was a direct flight, ANZ LOST MY bag and it took 4 days to find it and get it to me. Not fun.

The flight was smooth and on time. Entertainment options were lacking and there was no food, other than some very boring snacks.

A better selection of entertainment would have been nice. I found nothing that appealed to me as a middle-aged traveler. The flight attendants were gracious, helpful, and attentive. It also would have been nice to have more bathrooms as the flight was full and the plane was big.

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!

We had bulkhead seats in a A380 in the upper deck in seats 31 D and E. Storage was very limited other than in overhead bin - which is not within reach when in seat. Yet paying same price as others in premium economy who have a lot more storage within arm’s reach. Seems very unfair.

On the Qantas flight, I could barely hear some of the announcements. It was better when I could read them on the screen.

Good check in and helpful staff. Delayed for 1 hour. Took about 45 Mins to get baggage’s at DFW . Food was average ( Hindu meal ) . Overall it was good experience

Our boarding and flight was very good. However when we landed and pulled in to the gate it took 55 minutes for the jet bridge to be positioned next to the aircraft. That caused us to miss our ground transportation and it caused us unnecessary last minute transit planning and expense. Our flight was AA1733 on March 17, 2026

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.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

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

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

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.