SYD - CHI

$559 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 7/27. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$1,067
Typical prices: $1,557-$1,080
Multiple Airlines
Sat 7/25Sat 8/1
SYD - ORD • 2 stops
Cheapest one-way
$559
Typical prices: $868-$869
Multiple Airlines
Mon 7/27
SYD - ORD • 3 stops
Top airlines
Delta
Cheapest • from $1,069 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop 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 layover airports
Dallas (DFW)
Cheapest • Avg $1,010 (round-trip)
San Francisco (SFO)
Shortest trip • 19h 36m (one-way)
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 20% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 37% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s 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 round-trip 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 round-trip flight deals from Sydney to Chicago

Sat, Jul 25 - Sat, Aug 1
Multiple Airlines Logo
1:15 pm - 6:17 am
SYD
-
ORD
32h 02m
2 stops
Multiple Airlines Logo
9:28 am - 10:10 pm
ORD
-
SYD
45h 42m
3 stops
$1,067Multiple Airlines
Sun, Nov 15 - Sun, Nov 22
Delta Logo
10:40 am - 5:21 pm
SYD
-
ORD
23h 41m
1 stop
Delta Logo
2:55 pm - 8:30 am
ORD
-
SYD
24h 35m
1 stop
$1,069Delta
Sat, Oct 10 - Sat, Oct 31
Delta Logo
10:15 am - 1:47 pm
SYD
-
ORD
19h 32m
1 stop
Delta Logo
7:35 am - 7:30 am
ORD
-
SYD
31h 55m
1 stop
$1,123Delta
Thu, Nov 19 - Wed, Jan 6
Air New Zealand Logo
9:55 am - 10:36 pm
SYD
-
ORD
29h 41m
2 stops
Air New Zealand Logo
2:10 pm - 8:45 am
ORD
-
SYD
25h 35m
2 stops
$1,203Air New Zealand
Fri, Oct 9 - Thu, Oct 15
Etihad Airways Logo
4:40 pm - 3:40 pm
SYD
-
ORD
39h 00m
1 stop
Etihad Airways Logo
9:10 pm - 6:35 am
ORD
-
SYD
41h 25m
1 stop
$1,212Etihad Airways
Sat, Jul 25 - Sat, Aug 1
Multiple Airlines Logo
9:10 am - 6:17 am
SYD
-
ORD
36h 07m
1 stop
Multiple Airlines Logo
9:28 am - 7:05 am
ORD
-
SYD
30h 37m
2 stops
$1,224Multiple Airlines
Thu, Jul 16 - Sat, Aug 1
Multiple Airlines Logo
12:00 pm - 6:16 pm
SYD
-
ORD
21h 16m
1 stop
Multiple Airlines Logo
10:30 pm - 7:05 am
ORD
-
SYD
41h 35m
1 stop
$1,229Multiple Airlines
Thu, Nov 19 - Wed, Jan 6
Etihad Airways Logo
9:30 pm - 3:00 pm
SYD
-
ORD
34h 30m
1 stop
Etihad Airways Logo
8:20 pm - 5:55 pm
ORD
-
SYD
28h 35m
1 stop
$1,233Etihad Airways
Fri, Jul 24 - Tue, Aug 25
Air New Zealand Logo
7:50 am - 1:15 am
SYD
-
ORD
32h 25m
2 stops
Air New Zealand Logo
4:20 pm - 10:40 am
ORD
-
SYD
27h 20m
2 stops
$1,252Air New Zealand
Thu, Jul 16 - Wed, Jul 29
Multiple Airlines Logo
5:50 pm - 6:17 am
SYD
-
ORD
27h 27m
1 stop
Multiple Airlines Logo
6:00 am - 7:30 am
ORD
-
SYD
34h 30m
2 stops
$1,265Multiple Airlines
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 round-trip flight from Sydney to Chicago?

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

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 $468 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $920 and $865 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 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Find deals

Good to know

Low seasonMarch
Cheapest flight$559
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 8% increase in price.
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 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 Sydney to Chicago

  • What is the cheapest flight from Sydney to Chicago?

    In the last 5 days, the lowest price for a flight from Sydney to Chicago was $559 for a one-way ticket and $1,069 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Sydney and on arrival in Chicago.

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

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

  • Which airline alliances offer flights from Sydney to Chicago?

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

  • 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 round-trip 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 airline 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.
7.4
United AirlinesOverall score based on 9832 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

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

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

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.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Everything you need to know for your flight from Sydney to Chicago

Information on your arrival and departure airports

Sydney (SYD)