SYD - CHI

$876 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 19/7. 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
$1,336
Multiple Airlines
Mon 3/8Wed 19/8
SYD - MDW • 3 stops
Cheapest one-way flight
$876
Typical prices: $1,259-$1,260
Multiple Airlines
Sun 19/7
SYD - ORD • 3 stops
Top airlines
Cheapest • from $1,659 (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 $1,545 (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 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% 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

Mon, 3 Aug - Wed, 19 Aug
Multiple Airlines Logo
13:15 - 11:07
SYD
-
MDW
36h 52m
3 stops
Multiple Airlines Logo
06:05 - 11:50
MDW
-
SYD
38h 45m
3 stops
$1,336Multiple Airlines
Thu, 13 Aug - Thu, 20 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
09:20 - 11:50
ORD
-
SYD
35h 30m
3 stops
$1,350Multiple Airlines
Thu, 6 Aug - Tue, 11 Aug
Multiple Airlines Logo
06:15 - 09:51
SYD
-
MDW
42h 36m
3 stops
Multiple Airlines Logo
11:06 - 11:50
MDW
-
SYD
33h 44m
3 stops
$1,353Multiple Airlines
Mon, 3 Aug - Wed, 19 Aug
Multiple Airlines Logo
13:15 - 06:17
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
09:20 - 11:50
ORD
-
SYD
35h 30m
3 stops
$1,365Multiple Airlines
Thu, 13 Aug - Thu, 20 Aug
Multiple Airlines Logo
13:15 - 05:37
SYD
-
ORD
31h 22m
3 stops
Multiple Airlines Logo
09:20 - 11:50
ORD
-
SYD
35h 30m
3 stops
$1,462Multiple Airlines
Mon, 3 Aug - Wed, 19 Aug
Air New Zealand Logo
09:55 - 22:59
SYD
-
ORD
28h 04m
2 stops
Air New Zealand Logo
16:20 - 08:45
ORD
-
SYD
25h 25m
2 stops
$1,659Air New Zealand
Wed, 12 Aug - Wed, 19 Aug
Air New Zealand Logo
11:55 - 21:30
SYD
-
ORD
24h 35m
2 stops
Air New Zealand Logo
16:20 - 08:45
ORD
-
SYD
25h 25m
2 stops
$1,681Air New Zealand
Thu, 1 Oct - Fri, 9 Oct
Delta Logo
09:15 - 18:19
SYD
-
MDW
24h 04m
2 stops
Delta Logo
09:29 - 07:50
MDW
-
SYD
30h 21m
2 stops
$1,987Delta
Wed, 11 Nov - Sun, 15 Nov
Delta Logo
10:40 - 16:50
SYD
-
MDW
23h 10m
2 stops
Delta Logo
12:30 - 08:30
MDW
-
SYD
27h 00m
2 stops
$2,102Delta
Thu, 1 Oct - Fri, 9 Oct
Delta Logo
09:15 - 22:45
SYD
-
MDW
28h 30m
2 stops
Delta Logo
13:28 - 07:50
MDW
-
SYD
26h 22m
2 stops
$2,265Delta
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 $679 (return) on average. On the other hand, the most expensive months are February and January, where the average cost of round-trip tickets is $1,255 and $1,221 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 32% 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$876
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (13% 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 $876 for a one-way ticket and $1,336 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 $2,027 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 $1,534 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 649 reviews
7.9Comfort
7.4Entertainment
8.2Boarding
8.5Crew
7.4Food
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.

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

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.

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

Economy was much nicer on the Air New Zealand planes.

Couldn’t request a vegan meal somehow but I noticed other people getting them

They announced food service but then never came around. We also couldn’t land so kept trying to get to runway and then had to come up and go around happened like 3 times and cause the child next to me to start throwing up

Carring crew, nice ambiance of the cabin, comfortable beds, good food well served. We liked everything.

Great food and good entertainment options for the long flight.

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.

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

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.

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

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

I tried to check in online but was unable to do so. I stood in line for nearly two hours to check in. American Airlines was understaffed. When I finally got to the kiosk to check in, I was still unable to check in. No AA staff was available to help. Finally one of the airport security agents who was helping passengers became of lack of AA Staff told me: “I think the reason you can’t check in is that you are starting your name with an upper case letter when you write it. Just write it with all lower case letters.” That did allow me to check in. HOW COULD ANYONE POSSIBLY KNOW THAT IF THEY USE AN INITIAL UPPER CASE LETTER TO SPELL THEIR OWN NAME, AA WOULD NOT ALLOW THEM TO CHECK IN?????? Then I had to wait in line over half an hour again to drop off my baggage. Although I arrived at the airport 3 hours early, by the time I got to the gate, they had already started boarding.

Friendly staff, surprisingly good premium economy seats allowing good sleep/ snooze opportunity and very good menu.

The service was excellent. The quarters were a little cramped in Economy, and we had to exist there for 18 hours.

Food was great. Customer Service not so much! Flight Delays.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

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.

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.

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

I found the staff to not be very attentive at all. When paying for Business Class you expect a certain type of service and that was not found. They were almost rude even

Great. Food going from Australia to the US was better than other way around, but still needs improvement in terms of quality and quantity!!!

Due to a cancelled flight the day before this flight only had 44 people. Best flight ever on international route. Food getting better. Can United provide fruit ex apples and bananas for snacks? Crew fantastic.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

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 plane was comfortable but the crew wasn’t friendly.

I have been flying with American most of my professional career. But the airline seems tired and becoming more and more subpar with older planes than other airlines, dirtier and less comfortable seating, and less and less amenities. Their WiFi seldom works and their food is becoming more and more mediocre. How do you fly from LAX to PHL with only being offered one drink and as a platinum customer. I am exploring delta here on out for more of my flying.

American Airlines canceled the flight twice and was unable to facilitate a change of city for us after our travel plans became affected. We lost alot of money due to this and it seems like the airline was trying their best not to facilitate this. Mind you, I am a very loyal member.

Flight was a delayed a few minutes but nothing crazy, everything went extremely well

Our seats were better than i had anticipated. They provided nice pillows and blankets as well as a kit with ear plugs, sleep mask and headphones which made the long haul flight better. Their food selection and service was good. I appreciated that they came through the cabin with water a few times. We were ahead of schedule which was nice!

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.

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!

Full compliments to Captain for all four landing. Crew could be more polite and nice.

So smooth and easy! From boarding to arriving, we are very happy with our experience on air Canada.

There was a long delay on tarmac. The pilot kept us informed. The flight stewards were not entertaining or comforting. During the flight we received minimal service. Several food choices for purchase were not available at our seating of row 52. Only twice were we offered water for hydration. A half hour before landing teh pilot acknowledged that some passengers with connecting flights should tell flight stewards and they would help.. We had a connecting flight thand at should have had a 2+ hour layover and now would be less than 1 hour from departure. The flight attendant told us not to worry.. plenty of time. We did not get off the plane until after 6 o'clock. We are seniors (ages 74 and 72 ) and had to walk the length of the terminal to go thru customs and the length of the next terminal to departure gate for 6:30 a boarding call. We ran and were breathing hard and reached the departure gate by 6:50. We rate the flight stewards negatively...the pilot did his best.

It was very bad travelling with air canada the people working at check in bagages was very bad person any way I pay to much many to get good flights but it’s not

Air Canada switched my connecting flight to Alaska airlines without any communication to me. The process of finding this out, needing to leave one portion of the airport for the next and what i should have done with my luggage was not communicated to me at all. Even the Air Canada agent that noticed the airline switch at the terminal did not explain this process to me. In doing so my luggage did not arrive with me. The delay to create a claim too 2 hours.

Food was great. Staff was great. I would have liked to see more in flight shopping - they went by so fast I missed it. I would have liked more variety in tv shows but overall flight was great. The staff made all the difference.

The bathroom I used could have been cleaner and tidier. Didn't look like it was kept very well. The staff were super helpful. There was an issue with my screen, and they rebooted it for me. They were also great at dishing out our meals, and cleaning up after.

The seats were very nice. The flight attendants were obnoxious and rude. I felt that if I asked for something they would bite my head off! When I did ask for something, they said they would do it after they finished what they were doing, but never did. Horrible. Check in at business class took way too long.

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.