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CHI - SYD

$781 Find cheap flights from Chicago to Sydney

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Sydney departing on 8/22. 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
0 bags
Sat 7/6
Sat 7/13

Search hundreds of travel sites at once for deals on flights to Sydney

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sydney.
In the last 7 days travelers have searched 43,995,393 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Sydney (CHI-SYD)

 
These are the cheapest deals for flights from Chicago to Sydney currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Sydney

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Sydney.

Recent one-way flight deals from Chicago to Sydney

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Sydney found on KAYAK recently.

Recent last minute flight deals from Chicago to Sydney

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Sydney.

Recent direct flight deals from Chicago to Sydney

The latest deals for direct flights from Chicago to Sydney so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Sydney

Find recent round-trip train or bus tickets from Chicago to Sydney.

All round-trip flight deals to Sydney

The cheapest plane tickets to Sydney found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:31 pm - 6:35 amORD-SYD
26h 04m2 stops
9:25 am - 9:54 pmSYD-ORD
27h 29m2 stops
$1,121Delta
Find Deal
Wed, Sep 4 - Mon, Sep 16
1:10 pm - 7:35 amMDW-SYD
26h 25m2 stops
10:25 am - 5:59 pmSYD-MDW
23h 34m2 stops
$1,121Delta
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Wed, Oct 16 - Wed, Oct 23
4:50 pm - 8:45 amORD-SYD
24h 55m2 stops
11:50 am - 11:58 pmSYD-ORD
27h 08m2 stops
$1,203Air New Zealand
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Sun, Sep 1 - Wed, Sep 11
4:56 pm - 10:25 amORD-SYD
25h 29m2 stops
2:00 pm - 11:02 pmSYD-ORD
26h 02m2 stops
$1,228Air New Zealand
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Mon, Oct 28 - Mon, Nov 18
8:47 am - 8:20 amORD-SYD
31h 33m2 stops
10:20 am - 5:08 pmSYD-ORD
22h 48m2 stops
$1,242Air Canada
Find Deal
Tue, Oct 22 - Tue, Oct 29
7:20 am - 8:20 amORD-SYD
33h 00m3 stops
11:20 am - 7:56 amSYD-ORD
37h 36m2 stops
$1,248Air Canada
Find Deal
Mon, Oct 28 - Mon, Nov 18
9:51 am - 7:05 amORD-SYD
30h 14m1 stop
9:15 am - 11:57 pmSYD-ORD
29h 42m1 stop
$1,377Qantas Airways
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Mon, Aug 5 - Tue, Aug 13
2:23 pm - 7:05 amORD-SYD
25h 42m1 stop
9:15 am - 3:36 pmSYD-ORD
21h 21m1 stop
$1,398Qantas Airways
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Thu, Aug 8 - Thu, Aug 29
6:30 pm - 7:00 amORD-SYD
21h 30m1 stop
9:30 am - 6:54 pmSYD-ORD
24h 24m1 stop
$1,724United Airlines
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Tue, Jul 23 - Wed, Aug 14
12:49 pm - 7:00 amORD-SYD
27h 11m1 stop
10:20 am - 12:50 amSYD-ORD
29h 30m1 stop
$1,732United Airlines
Find Deal
Sun, Jun 16 - Sun, Jun 23
9:40 pm - 7:45 pmORD-SYD
31h 05m2 stops
Thu, Aug 22
8:26 pm - 7:45 pmORD-SYD
32h 19m2 stops
Tue, Aug 6
7:55 pm - 7:45 pmMDW-SYD
32h 50m2 stops
Tue, Aug 6
10:00 pm - 7:45 pmMDW-SYD
30h 45m2 stops
Thu, Aug 22
4:05 pm - 8:45 amORD-SYD
25h 40m1 stop
$944Cathay Pacific
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Tue, Aug 6
4:05 pm - 8:45 amORD-SYD
25h 40m1 stop
$960Cathay Pacific
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Thu, Aug 22
6:24 pm - 7:05 amORD-SYD
21h 41m1 stop
$1,242Qantas Airways
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Tue, Aug 6
10:55 am - 7:20 amORD-SYD
29h 25m3 stops
$1,444Air Canada
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Tue, Aug 13
10:35 am - 7:00 amORD-SYD
29h 25m2 stops
$1,529United Airlines
Find Deal
Fri, Jul 19
11:00 am - 9:20 amORD-SYD
29h 20m3 stops
$1,613Air Canada
Find Deal
Mon, Dec 2
8:26 pm - 7:45 pmORD-SYD
32h 19m2 stops
9:50 pm - 2:25 pmSYD-ORD
31h 35m1 stop
$1,874
Find Deal
Fri, Jun 7 - Wed, Jun 19
8:26 pm - 7:45 pmORD-SYD
32h 19m2 stops
10:05 am - 2:25 pmSYD-ORD
43h 20m1 stop
$1,891
Find Deal
Fri, Jun 7 - Mon, Jun 17
8:26 pm - 7:45 pmORD-SYD
32h 19m2 stops
9:50 pm - 2:25 pmSYD-ORD
31h 35m1 stop
$1,905
Find Deal
Fri, Jun 7 - Fri, Jun 21
8:47 am - 7:20 amORD-SYD
31h 33m2 stops
9:20 am - 2:21 pmSYD-ORD
20h 01m1 stop
$2,088Air Canada
Find Deal
Sat, Jun 8 - Sat, Aug 3
3:40 pm - 7:20 amORD-SYD
24h 40m1 stop
9:20 am - 2:21 pmSYD-ORD
20h 01m1 stop
$2,096Air Canada
Find Deal
Sat, Jun 8 - Sat, Aug 3
3:44 pm - 8:45 amORD-SYD
26h 01m2 stops
11:50 am - 11:59 pmSYD-ORD
27h 09m2 stops
$2,188Air New Zealand
Find Deal
Mon, Jun 10 - Wed, Jun 12
6:30 pm - 7:00 amORD-SYD
21h 30m1 stop
11:50 am - 11:59 pmSYD-ORD
27h 09m2 stops
$2,209Air New Zealand
Find Deal
Mon, Jun 10 - Wed, Jun 12
4:05 pm - 8:45 amORD-SYD
25h 40m1 stop
2:05 pm - 2:25 pmSYD-ORD
39h 20m1 stop
$2,540Cathay Pacific
Find Deal
Tue, Jun 11 - Mon, Jun 24
4:05 pm - 8:45 amORD-SYD
25h 40m1 stop
9:50 pm - 2:25 pmSYD-ORD
31h 35m1 stop
$2,575Cathay Pacific
Find Deal
Tue, Jun 11 - Sat, Jun 22
5:07 pm - 7:05 amORD-SYD
22h 58m1 stop
9:15 am - 3:55 pmSYD-ORD
21h 40m1 stop
$2,679Qantas Airways
Find Deal
Mon, Jun 10 - Wed, Jun 12

Flights from Chicago to Sydney - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Sydney to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Sydney?

The average price of all flights from Chicago to Sydney clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to Sydney, you should consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Chicago to Sydney?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Sydney, 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 Chicago to Sydney is February, where tickets cost $1,195 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $2,143 and $1,768 respectively.

How far in advance should I book a flight from Chicago to Sydney?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Sydney, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Sydney, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 28 days before departure.

Which airlines provide the cheapest flights from Chicago to Sydney?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on China Southern ($902) and Cathay Pacific ($944). The cheapest round-trip tickets were found on Delta ($1,121) and Air New Zealand ($1,203).

Good to know

Low season

October

High season

December

Cheapest flight

$781
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 39% increase in price.
Flight from Chicago O'Hare Airport to Sydney

When to book flights from Chicago to Sydney

Are your dates flexible? Find out the best times to travel from Chicago to Sydney 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 Chicago to Sydney

  • Can I fly directly from Chicago to Sydney?

    Unfortunately, there aren’t any airlines with a direct connection from Chicago to Sydney. Your trips will involve at least one layover, with certain airlines even having two layovers scheduled for this trip. The location of the layover will depend on the airline you’re flying with. For instance, Air New Zealand has its layovers scheduled for Auckland while Air India has Delhi. Both American Airlines and United have Los Angeles as the set layover destination for this route.

  • Is public transport available from Sydney Airport (SYD) to downtown Sydney?

    Yes, there is a train that connects the airport to the city center. It is the cheapest option available and also the quickest, taking the best part of fifteen minutes between the airport and downtown. However, it is not as convenient as a taxi especially when you have a lot of luggage as it will drop you off at the Circular Quay in the center of Sydney then you will have to walk to your hotel.

  • What are the benefits of upgrading to first class for this trip?

    For a long flight like this one, you are sure to get maximum value for your money when you upgrade to first class. The seats are much more comfortable, making the trip more bearable, and you can stretch out freely with the extra legroom. In addition, you will be served an amazing selection of meals and drinks to enjoy at various points during the flight. Lastly, you will be able to access the first-class lounges during your layover, where you can freshen up and get some rest while waiting for the second leg of the flight.

  • Do I need a visa to fly from Chicago to Sydney?

    Yes, a visa is one of the mandatory requirements for all US citizens going to Sydney or any other Australian city. As they don’t provide any visas on arrival, you have to apply beforehand by visiting the Embassy or Consulate in advance of your travel dates to ensure that they have been processed by the time you’re flying out. You can also apply for an ETA via an online process, which is much more convenient.

  • What is the cheapest flight from Chicago to Sydney?

    In the last 3 days, the lowest price for a flight from Chicago to Sydney was $781 for a one-way ticket and $1,121 for a round-trip.

  • Do I need a passport to fly between Chicago and Sydney?

    Yes, you’ll need a passport to travel to Sydney from Chicago.

  • Which airports will I be using when flying from Chicago to Sydney?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Sydney Kingsford Smith is the only airport in Sydney. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Sydney?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Sydney?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Sydney, with Star Alliance being the most commonly used for this route.

  • What is the most popular layover when flying to Sydney from Chicago?

    Los Angeles is the most popular layover city among KAYAK users traveling from Chicago to Sydney.

  • Which is the best airline for flights from Chicago to Sydney, ANA or Air New Zealand?

    The two airlines most popular with KAYAK users for flights from Chicago to Sydney are ANA and Air New Zealand. With an average price for the route of $2,131 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 $1,682 and an overall rating of 8.1.

  • How does KAYAK find such low prices on flights from Chicago to Sydney?

    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 Chicago to Sydney.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Sydney?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sydney from Chicago 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 Chicago to Sydney?

    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 Sydney with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Sydney?

    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 Sydney from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Sydney

  • Air New Zealand is a great option to book when flying with the entire family. They have free Wi-Fi available plus seatback on-demand video and free meals, all of which should make it a better experience for the kids.
  • The Blue Line train from downtown Chicago to O’Hare International Airport (ORD) is a good commuter option when you want to avoid the rush hour traffic that is usually quite a menace.
  • United Airlines doesn’t allow passengers to bring carry-on bags to the economy class cabin. However, they do allow one checked bag for free, meaning if you have any bags, you will need to check them before the flight.
  • American Airlines offers travelers the chance to calculate and offset the emissions generated during the flight from Chicago to Sydney through Cool Effect. This is a great way to make your trips more sustainable and keep the carbon footprint low.
  • Chicago Midway is an alternative departure airport to O’Hare. It is closer to downtown Chicago and also less busy, however, there are few flight options from the airport with all of them being served by Delta and including at least two layovers.
See more tips

Top 5 airlines serving from Chicago to Sydney

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sydney. 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 Chicago to Sydney? 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.
8.1
Air New ZealandOverall score based on 603 reviews
8.4Boarding
8.7Crew
7.9Entertainment
8.1Comfort
7.6Food
Airline reviews

Can you please process refund. Mum died and dad went to Pakistan to bury her after cancelling flight.

2.0 MediocreAnonymous, May 2024AKL - YVR
Read more about Air New Zealand reviews

Can you please process refund. Mum died and dad went to Pakistan to bury her after cancelling flight.

Short flight so no entertainment, turbulence so no food service - overall flight as expected

All was good, the only thing was it didn't run on time.

Overall excellent but the Captain kept the seat belt sign on for far too long, especially at the beginning and end of the flight. It was 2 hours after take-off before the crew were able to start the service (on an 11 hour night flight, reducing our sleeping time) and the seat belt sign on went on during breakfast (90 mins before landing) and was not turned off again until we landed. This made for an uncomfortable journey of trying to limit fluid intake because it was unclear when the toilets would be available for use.

The staff and crew on board were excellent. Business class however, was very weird. I thought we would have individual pods, but the way it was set up was unexpected. Not very private and If you wanted to lay down, you had to have an entire bed made up for you by the crew, rather than how Delta one works where you could just lie down whenever you feel like it. It was a 16 hour flight. I chose not to have my bed made, and that turned out to be a good idea because everybody who had their bed made had to wait for the crew to roll up their mattresses. So strange!

Food was not good. We asked for Muslim food and it was weird tasteless type of boiled veges.

Crew were pleasant, happy to be there and were a joy to be around. Entire operation was professional, well thought out and ran like a Swiss clock.

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

United flight from SFO to PDX was cancelled. I will ask for a refund. Had to book on Alaska

The recline on the seat in front of me came back so that I was staring at the top of the man’s head in front of me the whole trip. He refused to bring his seat back up twice every time he was instructed to do so and only relented when he had a tray of good in front of him. And then right back in my lap!!! Horrible man!! I complained to the staff multiple times, but no one would address the issue. Otherwise, it would have been a perfect flight.

The seats are too close together and are smaller than they used to be. Makes for a cramped experience.

The international flight from Sydney to Dallas had great food. I have travelled a lot over the years and this has been the most memorable in my experience so far.

flight delayed, wait in crowded gate. staff inattentive. had to remind them to get my coat from their closet. not many new movies, media choices were limited (nothing compared to Emirates.) Lounge was crowded

flight delayed, wait in crowded gate. staff inattentive. had to remind them to get my coat from their closet. not many new movies, media choices were limited (nothing compared to Emirates.)

Initial flight was cancelled so moved to an alternative flight. As a result, stuck in a middle seat. Flight then place in holding pattern prior to landing resulting in a very late trip home.

There was nothing I didn’t like, prices a little lower would help

Flight delay was informed at the last minute. Food quality is not up to Qantas standard I was unable to book an online boarding pass on any of my 6 flights.

Following a marathon flight riddled by delays and changes from Santiago, Chile, my flight to Melbourne from Sydney was on schedule but I was transferred to the next flight. The reason by ticketing and the floor manager was I missed the entry to flight by one minute! That's right, the emphasised that if I was 1 minute earlier I would be on the flight. I asked what was the point them emphasising 1minute overdue and how that helped me or the situation. They didn't care at all. Replying that if it was one minute earlier they would've done something and smirking delivering the information. Australian's do call Australia home, Qantas calls Australian's suckers.

Rescheduled after ticket purchased and issued, not 2 or 3 times and not a fourth but by 5 times, by Qantas, that's right, 5 changes! Forcing an overnight stay in Chile and need for visa. Qantas can no longer provide basic services as a national or international service provider. Professionalism is extinct and the provider needs to be mentored and educated in perfecting who to operate as an airline. Qantas is the spirit of Australian dissatisfaction.

Amazing! Was put on the earlier flight and I requested for an aisle seat and was given it. Thanks Qantas!

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

The food at Admirals Club was really great Pijamas were a nice feature The flight attendant was very nice and great attitude The aa.com does not work well specially internet service Overall a very good flight .

No seat assignment . Last on board . Though I would not receive any boarding pass

last minute was rebooked. This rebooking made me miss my connection, added a stop in my itinerary without my approval, and had me arriving 10 hours later to my destination...for a delay that was 2 hours. To boot, my final flight from London to Athens booked me in a middle seat, where I originally booked all aisle seats. This was incredibly uncomfortable for a 24 hour journey and made me incredibly upset.

Did not appreciate “hidden fees” to check a bag for international flight and purchase a seat to be next to my spouse. Won’t choose this airline again.

The flight left over 2 hours late and caused me to miss my connecting flight. Consequently, I missed my cruise ship out of Barcelona. The cost associated with this miss was as follows: Airfare to Sicily Italy to get on the ship TWO days late - $232.30 Taxi from Airport to hotel $35 Dinner at hotel $38 Hotel in Barcelona - $208 Taxi from Sicily to hotel $70 Hotel in Sicily - $148 Prorated time missed on cruise $ 1,143

No meal. Flight crew was wonderful, happily finding me storage for my guitar. THANK YOU!!!

My seat was moved multiple times. I picked out the perfect seats beforehand. I even paid extra money for them. However, I was moved to a middle seat without warning at the last minute. It was like my worst nightmare. But other than that, the actual flight was good. Everything was on time or even early and the flight was smooth.

A220 plane had 5 seats across which is great for couples who can snag the A&C seats. Seat itself is borderline comfortable but still tough on a 5+ hour flight. Overhead bins are small so if you're not in at least boarding group 5, you could be in trouble. No included food service. Non-alcoholic drinks are free but even the most basic snacks are for a charge. Price was reasonable for the only direct SEA-YUL flight. Boarding is efficient even managing passport checks. Worth flying for the direct flight.

The original flight from Boston to Toronto was canceled because of a mechanical failure. I was then scheduled on a flight to go from Boston to Montreal and then Montreal to Toronto. The flight was extremely full and I had to check my carry-on bag. When I actually got on the plane there appeared to be room for my bag. I understand the mechanical failures happen. But it was frustrating that they pestered me to check my bag when I don't believe it was necessary. Additionally, not just with Air Canada, modern airline seats are incredibly uncomfortable. There is considerable research that shows that the shape of them is poor for back health.

Unable to initiate refund/reschedule the ticket #worst experience #lost 900$

Flight was delayed for almost 3 hours. Communication of gate change was poor. Email and screen said one gate and it was a different gate from that. Gate changed first to 64 B and then to 64 C. Originally it was 68B. 64C was not communicated properly!

Book cheap flights from Chicago to Sydney

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Sydney found on KAYAK in the last 72 hours.
8/22Thu
2 stops
31h 05mORD-SYD
$781
8/6Tue
2 stops
32h 19mORD-SYD
$813
8/6Tue
2 stops
32h 50mMDW-SYD
$813
8/22Thu
2 stops
30h 45mMDW-SYD
$826
8/6Tue
1 stopCathay Pacific
25h 40mORD-SYD
$944
8/22Thu
1 stopCathay Pacific
25h 40mORD-SYD
$960
8/6Tue
1 stopQantas Airways
21h 41mORD-SYD
$1,242
8/13Tue
3 stopsAir Canada
29h 25mORD-SYD
$1,444
7/19Fri
2 stopsUnited Airlines
29h 25mORD-SYD
$1,529
12/2Mon
3 stopsAir Canada
29h 20mORD-SYD
$1,613

Search by stops

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Last minute flights from Chicago to Sydney

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Sydney that are departing in the next 10 days.
6/7Fri
multi-stop
32h 19mORD-SYD
6/19Wed
multi-stop
31h 35mSYD-ORD
$1,874
6/7Fri
multi-stop
32h 19mORD-SYD
6/17Mon
multi-stop
43h 20mSYD-ORD
$1,891
6/7Fri
multi-stop
32h 19mORD-SYD
6/21Fri
multi-stop
31h 35mSYD-ORD
$1,905
6/8Sat
multi-stopAir Canada
31h 33mORD-SYD
8/3Sat
multi-stopAir Canada
20h 01mSYD-ORD
$2,088
6/8Sat
multi-stopAir Canada
24h 40mORD-SYD
8/3Sat
multi-stopAir Canada
20h 01mSYD-ORD
$2,096
6/10Mon
multi-stopAir New Zealand
26h 01mORD-SYD
6/12Wed
multi-stopAir New Zealand
27h 09mSYD-ORD
$2,188
6/10Mon
multi-stopAir New Zealand
21h 30mORD-SYD
6/12Wed
multi-stopAir New Zealand
27h 09mSYD-ORD
$2,209
6/11Tue
multi-stopCathay Pacific
25h 40mORD-SYD
6/24Mon
multi-stopCathay Pacific
39h 20mSYD-ORD
$2,540
6/11Tue
multi-stopCathay Pacific
25h 40mORD-SYD
6/22Sat
multi-stopCathay Pacific
31h 35mSYD-ORD
$2,575
6/10Mon
multi-stopQantas Airways
22h 58mORD-SYD
6/12Wed
multi-stopQantas Airways
21h 40mSYD-ORD
$2,679

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Flights to Sydney

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Sydney (SYD)Australia

Return flight deals:

Sydney - Chicago

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