SYD - CHI

$956 Find Cheap Flights from Sydney to Chicago – Compare and Save

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 12/8. 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.
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
$1,321
Typical prices: $1,506-$1,937
Multiple Airlines
Wed 12/8Wed 19/8
SYD - ORD • 2 stops
Cheapest one-way flight
$956
Typical prices: $1,115-$1,838
Multiple Airlines
Wed 12/8
SYD - ORD • 3 stops
Top airlines
Cheapest • from $1,506 (return)
Best reviews • 8.0 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 $1,534 (return)
Shortest trip • 20h 02m (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 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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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

Wed, 12 Aug - Wed, 19 Aug
Multiple Airlines Logo
06:05 - 06:17
SYD
-
ORD
39h 12m
2 stops
Multiple Airlines Logo
09:20 - 11:50
ORD
-
SYD
35h 30m
3 stops
$1,321Multiple Airlines
Mon, 3 Aug - Mon, 17 Aug
Multiple Airlines Logo
13:15 - 11:07
SYD
-
MDW
36h 52m
3 stops
Multiple Airlines Logo
11:06 - 11:50
MDW
-
SYD
33h 44m
3 stops
$1,368Multiple Airlines
Mon, 27 Jul - Mon, 10 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
10:16 - 11:50
ORD
-
SYD
34h 34m
3 stops
$1,406Multiple Airlines
Mon, 3 Aug - Mon, 17 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
07:15 - 11:50
ORD
-
SYD
37h 35m
3 stops
$1,421Multiple Airlines
Mon, 27 Jul - Mon, 10 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
10:16 - 11:50
ORD
-
SYD
34h 34m
3 stops
$1,450Multiple Airlines
Mon, 3 Aug - Mon, 10 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
10:16 - 22:10
ORD
-
SYD
44h 54m
3 stops
$1,457Multiple Airlines
Sat, 5 Sep - Sun, 6 Sep
Qantas Airways Logo
17:50 - 14:54
SYD
-
ORD
36h 04m
1 stop
Qantas Airways Logo
17:05 - 06:25
ORD
-
SYD
22h 20m
1 stop
$1,506Qantas Airways
Wed, 11 Nov - Mon, 16 Nov
Air New Zealand Logo
09:55 - 21:34
SYD
-
ORD
28h 39m
2 stops
Air New Zealand Logo
13:00 - 10:30
ORD
-
SYD
28h 30m
2 stops
$1,573Air New Zealand
Thu, 3 Sep - Sun, 20 Sep
Delta Logo
09:15 - 18:33
SYD
-
MDW
24h 18m
2 stops
Delta Logo
09:29 - 06:50
MDW
-
SYD
30h 21m
2 stops
$1,689Delta
Wed, 9 Dec - Thu, 14 Jan
Delta Logo
10:40 - 22:10
SYD
-
MDW
28h 30m
2 stops
Delta Logo
12:30 - 08:30
MDW
-
SYD
27h 00m
2 stops
$2,116Delta
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 August.

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 December, where tickets cost $674 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $1,325 and $1,246 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 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$956
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (8% 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 $956 for a one-way ticket and $1,321 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 $2,013 and an overall rating of 8.3, ANA is the most popular choice. Air New Zealand is also a great choice for the route, with an average price of $1,522 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.
8.0
Air New ZealandOverall score based on 645 reviews
7.9Comfort
7.4Entertainment
8.2Boarding
7.4Food
8.5Crew
Airline reviews

We got to experience Premium Economy from Sydney to Auckland and it was a great experience wiht Air New Zealand. The crew was friendly and helpful.

10.0 ExcellentManish, May 2026
SYD - AKL
Read more Air New Zealand reviews

We got to experience Premium Economy from Sydney to Auckland and it was a great experience wiht Air New Zealand. The crew was friendly and helpful.

Great airline service by the staff. I highly recommend it

Needed more leg room. Leg rest and entertainment system box took up a lot of space and I'm not tall. Breakfast was good. Poor quality of the entertainment options.

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.

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.

We had a cancellation due to weather, but the American Airlines staff was very helpful. Once we got on a plane, the trip was great.

Great food and good entertainment options for the long flight.

It seems that qantas are trying hard to regain their status as Australia's premier airline. I only flew economy but happy with the service entertainment, food, configuration everything.

Loved the food and beverages available, spacious economy class, excellent entertainment

Very good overall. Highly recommend for all flying to Australia

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.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

Uncomfortable plastic seats even in premium economy. No free wifi. Even paid wifi was spotty to nonexistent. Bad food. Much worse than economy on foreign carriers like Qantas.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The plane was comfortable but the crew wasn’t friendly.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

check in for premium economy very nice. Friendly attendants. Best security video ever. Seriously. That's about it. Not a good bang for the premium economy buck, to be truthful. I had hoped/expected for a little more.

Delayed 2 and a half hours Middle seat next to a majorly overweight guy who took up most of my seat

Smooth ride but I wish they have better food selections.

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

Multiple delays and gate changes resulting in arrival with a 5 hour delay.

One crew member, Brandy was very helpful with recovering phone lost in customs. The plane was ancient and poorly maintained. Checked baggage did not arrive with flight. Almost missed flight because if insanely short layover time. Air Canada is worst flight I have ever booked with Kayak. Wanted to charge for headsets for on flight media.

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.

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

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.