853 € Cheap Flights from Sydney to Chicago

Compare Sydney to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Sydney to Chicago

Looking for a cheap last-minute deal or the best return flight from Sydney to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Sydney to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Sydney to Chicago flights are currently cheapest in November.

Alternative Sydney to Chicago routes

Looking for the cheapest, fastest or easiest route from Sydney to Chicago? You could fly into the following airports instead.

Sydney to Chicago: Flight information

The things to know before you go.
Cheapest flight found853 €
Cheapest month to flyOctober

Finding cheap flights from Sydney to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Sydney to Chicago is 853 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Sydney to Chicago. But we found flights with one or more stops from 853 €.
As of September 2025, there are no flights flying from Sydney to Chicago.
The cheapest month to fly from Sydney to Chicago is usually October.
If you're flying from Sydney Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 853 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago on Friday, 17 October 2025.
No airlines currently offer direct flights between Sydney Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In September, the average temperature is usually around 18°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Jetstar offers the cheapest flight tickets to Chicago.

Travelling from Sydney (Kingsford Smith) Airport (SYD) to Chicago: what you need to know

  • Chicago is 16 hours behind Sydney, where Sydney (Kingsford Smith) Airport is located. Chicago runs on the UTC-5 timezone.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your SYD to Chicago flight.

  • Delays at check-in and security are likely if you're jetting off during high season, so allow some extra wiggle room. A good general rule for peak times? Get there up to four hours early for international flights and at least two hours for domestic departures.

  • A stopover is the perfect opportunity to take a break from travelling and possibly even explore another city. When searching for plane tickets from SYD to Chicago, uncheck the 'Direct flights only' box to see where you can stop along the way. Consider one of these popular options:

    • Dallas/Fort Worth International Airport (DFW)

    • Los Angeles International Airport (LAX)

    • San Francisco International Airport (SFO)

  • Travelling from central Sydney to SYD takes about 25 minutes by public transport. If you drive, ride-share or take a cab, you'll cover the 8 kilometres in 20 minutes or so, depending on traffic.

  • Want a hassle-free start to your travels? Stay near SYD. Whether you're catching an early flight from Sydney (Kingsford Smith) Airport to Chicago or just don't like being rushed, these hotels are worth a look:

  • Of all flights departing from Sydney (Kingsford Smith) Airport, 69.62% land on time at their destination.

How to find the cheapest flights from Sydney (Kingsford Smith) Airport (SYD) to Chicago

  • 381 € is currently the lowest price for a one-way Sydney (Kingsford Smith) Airport to Chicago flight. A return plane ticket starts from 853 €. These prices may change based on demand.

  • To find cheap flights from SYD to Chicago, book as early as you can. Airlines generally offer lower prices when flights first go on sale.

  • The 'Whole month' tool will show you the cheapest tickets from Sydney (Kingsford Smith) Airport to Chicago throughout the entire month. It's a good way to snap up a bargain if your trip dates are flexible.

  • Locking in a cheap flight from SYD to Chicago couldn't be easier with Price Alerts. Simply set up one of these automatic notifications and we'll let you know as soon as a cheaper option becomes available.

  • Tailor your flights with filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Sydney (Kingsford Smith) Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from the centre of Chicago. If you're grabbing a cab or a ride-share, the drive takes roughly 35 minutes.

  • When travelling by public transport, expect a journey time of around 55 minutes.

  • Consider booking a hotel close to ORD if you're coming in on a late flight from Sydney (Kingsford Smith) Airport to Chicago. Pick one of these accommodation options and avoid the hassle of a long transfer:

  • Pick up an O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers to choose from here.

  • Booking your vehicle from O'Hare International Airport around four weeks before your flight from SYD to Chicago can help you lock in the best possible rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Sydney (Kingsford Smith) Airport to Chicago has hit the runway and you've navigated your way to arrivals, the drive should take about 20 minutes.

  • If you travel by public transport, the ride to the centre will take you 45 minutes or so.

  • Following your SYD to Chicago flight, unwind at a hotel near MDW. These are some comfortable options that'll help you sink into relaxation mode:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car simple. These providers are located in or around the terminal and will have you on your way in a heartbeat.

  • Lock in the lowest price by booking your ride from MDW four weeks in advance. You'll also have access to a wider range of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Sydney (Kingsford Smith) Airport to Chicago and make your way to your hotel or start sightseeing right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach driving.

  • Public transport will take you there in about 4 hours 15 minutes.

  • Reserve a hotel near RFD and go from landing to lounging in your room in a flash. Whether you're arriving on a late SYD to Chicago flight or just want to keep your travel plans simple, these accommodation options offer convenience when you need it most:

  • Begin your travels without stressing over how to reach your destination with a Chicago Rockford International Airport rental car. You can book your wheels with reliable names here like Budget, Alamo and National.

  • If you'd like a certain make or model, booking early gives you a better shot at getting your first choice. Secure your ride from RFD a few weeks ahead of your flight from Sydney (Kingsford Smith) Airport to Chicago.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Visit Chicago in high season if you prefer a busy atmosphere, but remember that hotel prices are generally higher. Alternatively, book flights from Sydney (Kingsford Smith) Airport to Chicago during low season when prices are cheaper and it's not as busy.

  • Book a Sydney (Kingsford Smith) Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. Expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from SYD to Chicago around that time if you like cooler conditions.

More about Chicago

Explore more of United States

  • Chicago has plenty to offer, but there are so many other corners of United States you should also see. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Get a taste of what this destination has to offer at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.