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Cheap Flights from Sydney to Chicago

Travellers and cabin class

Compare Sydney to Chicago flight deals

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

Book the best Chicago fare with no extra fees

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.
Chicago.SAR 2,072 per passenger.Departing Fri, 30 May.One-way flight with Jetstar.Outbound indirect flight with Jetstar, departs from Sydney on Fri, 30 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,072, select.
Chicago.SAR 2,154 per passenger.Departing Thu, 12 Jun.One-way flight with Jetstar.Outbound indirect flight with Jetstar, departs from Sydney on Thu, 12 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,154, select.
Chicago.SAR 2,254 per passenger.Departing Fri, 5 Sep.One-way flight with Jetstar.Outbound indirect flight with Jetstar, departs from Sydney on Fri, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,254, select.
Chicago.SAR 2,291 per passenger.Departing Fri, 14 Nov.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Fri, 14 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,291, select.
Chicago.SAR 2,295 per passenger.Departing Sun, 20 Jul.One-way flight with Jetstar.Outbound indirect flight with Jetstar, departs from Sydney on Sun, 20 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,295, select.
Chicago.SAR 2,360 per passenger.Departing Fri, 31 Oct.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Fri, 31 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,360, select.
Chicago.SAR 2,456 per passenger.Departing Thu, 14 Aug.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Thu, 14 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,456, select.
Chicago.SAR 2,902 per passenger.Departing Thu, 11 Dec.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Thu, 11 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,902, select.

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.
May
from SAR 2,072
Jun
from SAR 2,154
Jul
from SAR 2,295
Aug
from SAR 2,456
Sep
from SAR 2,254
Oct
from SAR 2,360
Nov
from SAR 2,291
Dec
from SAR 2,902
Jan
from SAR 3,841
Feb
Find prices
Mar
from SAR 3,184
Apr
Find prices

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 foundSAR 2,072
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 SAR 2,956. 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 SAR 2,956.
As of May 2025, there are no flights flying from Sydney to Chicago.
The cheapest month to fly from Sydney to Chicago is usually May 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 SAR 2,956.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago on Tuesday, 3 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 May, the average temperature is usually around 13°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, United offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Sydney

Looking for cheap tickets from Sydney to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Sydney to Chicago. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from Sydney from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best Sydney-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Sydney.
  • Set up a Price Alert. You can easily track the fare of your cheap Sydney-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Sydney and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Sydney and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Sydney to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

    • Combine your flight to Chicago from Sydney with hotels and car hire

    Once you've secured your cheap flight ticket from Sydney to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


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Plan the rest of your trip from Sydney to Chicago

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