Cheap Flights from Sydney to Chicago

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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 May.

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 foundRs142,940
Cheapest month to flyMay

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 Rs262,462. 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 Rs262,462.
As of April 2025, there are no flights flying from Sydney to Chicago.
The cheapest month to fly from Sydney to Chicago is usually April 2025.
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 Rs262,462.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago on Thursday, 5 June 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 April, the average temperature is usually around 8°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, Fiji Airways offers the cheapest flight tickets to Chicago.

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

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

  • To ensure you catch your flight from SYD to Chicago, leave enough time to navigate the airport and find your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • You'll likely experience longer queues in popular months such as July and other peak periods. Arriving up to four hours in advance for international flights and two hours for domestic departures is a good idea.

  • Think about adding a stopover to possibly find a cheaper flight from SYD to Chicago. Simply uncheck 'Direct flights only' when browsing the departures. Break up your trip (and maybe save some cash) by stopping at one of these popular airports:

    • Los Angeles International Airport (LAX)

    • Dallas/Fort Worth International Airport (DFW)

    • San Francisco International Airport (SFO)

  • To enter United States for tourism purposes, you will need an ETA if you have a passport from Australia. However, visa rules are subject to change and you may need other documents depending on the duration and purpose of your trip. Always check the most up-to-date guidelines before booking your cheap ticket from Sydney (Kingsford Smith) Airport to Chicago.

  • Located around 18 kilometres from the centre of Sydney, SYD can be reached in about 21 minutes by car (depending on traffic). The journey by public transport is roughly 27 minutes.

  • After a leisurely start to your journey? Stay near SYD. Whether you're catching an early flight from Sydney (Kingsford Smith) Airport to Chicago or just don't want to be rushed, these hotels are ideal:

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

  • The lowest price we've found for a one-way ticket from Sydney (Kingsford Smith) Airport to Chicago is Rs142,940. The cheapest price for a return flight is Rs262,462. Keep in mind fares can change due to demand at the time of booking.

  • To find cheap tickets from SYD to Chicago, book early. Airlines typically offer lower fares when flights are first made available.

  • If you're willing to be flexible with your travel plans, try using the 'Whole month' tool. It'll show you the lowest price in each month when searching for your ticket from Sydney (Kingsford Smith) Airport to Chicago.

  • Sign into your online account or use the app to create a Price Alert. We'll notify you right away if there's a better deal on this route. It's simple to do, and it'll save you time looking for flight tickets from SYD to Chicago every day.

  • Make the most of the filters to find your ideal journey. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Sydney (Kingsford Smith) Airport to Chicago, use the 'Sort by' tool. You can also filter by airline, arrival and departure times, and number of stops.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the most popular month to board a flight from Sydney (Kingsford Smith) Airport to Chicago while February is the quietest. To work out the best time to go to Chicago, consider your preferred travel pace and style.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Lock in your flights from Sydney (Kingsford Smith) Airport to Chicago in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from SYD to Chicago sometime then if you like travelling in cooler conditions.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the perfect place to stay. After booking your flight from Sydney (Kingsford Smith) Airport to Chicago, browse our selection of hotels including:

  • There are so many things to discover in this city it can be difficult to know where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are top sights which should feature on any well-planned Chicago itinerary.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Sydney (Kingsford Smith) Airport to Chicago to track down amazing deals on car rentals. Search for your ride in seconds and compare offers in one place. Plus we give you everything you need to know about car rentals in Chicago, from the most popular rental company to the best time to book.

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