Cheap Flights from Sydney to Chicago O'Hare International

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Compare Sydney to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

Book the best Chicago O'Hare International fare with no extra fees

Flight deals Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Sydney to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Sydney Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from $1,719. Find the lowest prices on one-way and return tickets right here.

Chicago.$1,719 per passenger.Departing Mon, 5 Oct, returning Mon, 19 Oct.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Mon, 5 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 19 Oct, arriving in Sydney.Price includes taxes and charges.From $1,719, select.

Chicago.$1,752 per passenger.Departing Mon, 26 Apr, returning Mon, 17 May.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Mon, 26 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 17 May, arriving in Sydney.Price includes taxes and charges.From $1,752, select.

Chicago.$1,752 per passenger.Departing Mon, 1 Mar, returning Mon, 15 Mar.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Mon, 1 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 15 Mar, arriving in Sydney.Price includes taxes and charges.From $1,752, select.

Chicago.$1,752 per passenger.Departing Tue, 20 Oct, returning Mon, 2 Nov.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Tue, 20 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 2 Nov, arriving in Sydney.Price includes taxes and charges.From $1,752, select.

Chicago.$1,752 per passenger.Departing Tue, 6 Apr, returning Tue, 20 Apr.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Tue, 6 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Tue, 20 Apr, arriving in Sydney.Price includes taxes and charges.From $1,752, select.

Chicago.$1,754 per passenger.Departing Mon, 16 Nov, returning Mon, 7 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Mon, 16 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Sydney.Price includes taxes and charges.From $1,754, select.

Chicago.$1,762 per passenger.Departing Tue, 16 Feb, returning Sun, 21 Feb.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Tue, 16 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sun, 21 Feb, arriving in Sydney.Price includes taxes and charges.From $1,762, select.

Chicago.$1,799 per passenger.Departing Thu, 5 Nov, returning Mon, 25 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Thu, 5 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 25 Jan, arriving in Sydney.Price includes taxes and charges.From $1,799, select.

Chicago.$1,800 per passenger.Departing Thu, 28 Jan, returning Mon, 1 Feb.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Thu, 28 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 1 Feb, arriving in Sydney.Price includes taxes and charges.From $1,800, select.

Chicago.$1,800 per passenger.Departing Thu, 5 Nov, returning Thu, 19 Nov.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Thu, 5 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Thu, 19 Nov, arriving in Sydney.Price includes taxes and charges.From $1,800, select.

Chicago.$1,806 per passenger.Departing Wed, 7 Oct, returning Wed, 26 May.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Wed, 7 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 26 May, arriving in Sydney.Price includes taxes and charges.From $1,806, select.

Chicago.$1,813 per passenger.Departing Thu, 18 Feb, returning Wed, 3 Mar.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Thu, 18 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 3 Mar, arriving in Sydney.Price includes taxes and charges.From $1,813, select.

Chicago.$1,814 per passenger.Departing Tue, 4 May, returning Wed, 12 May.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Tue, 4 May, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 12 May, arriving in Sydney.Price includes taxes and charges.From $1,814, select.

Chicago.$1,879 per passenger.Departing Tue, 1 Jun, returning Wed, 28 Jul.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Tue, 1 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 28 Jul, arriving in Sydney.Price includes taxes and charges.From $1,879, select.

Chicago.$1,893 per passenger.Departing Fri, 26 Mar, returning Tue, 6 Apr.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Fri, 26 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Tue, 6 Apr, arriving in Sydney.Price includes taxes and charges.From $1,893, select.

Chicago.$1,917 per passenger.Departing Sun, 24 Jan, returning Sun, 31 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Sydney on Sun, 24 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sun, 31 Jan, arriving in Sydney.Price includes taxes and charges.From $1,917, select.

Find the cheapest month to fly from Sydney to Chicago O'Hare International

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

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Sydney to Chicago O'Hare International: Alternative routes

Compare routes from Sydney to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Sydney to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$1,719
Cheapest month to fly	October

Finding cheap flights from Sydney to Chicago O'Hare International: Frequently asked questions

How much are return flights from Sydney to Chicago O'Hare International?

The best price we found for a return flight from Sydney to Chicago O'Hare International is $1,719. 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.

Which airlines fly direct from Sydney to Chicago O'Hare International?

Currently, there are no airlines that fly direct from Sydney to Chicago O'Hare International. But we found flights with one or more stops from $1,719.

How many flights are there a week from Sydney to Chicago O'Hare International?

As of September 2026, there are no flights flying from Sydney to Chicago O'Hare International.

When is the cheapest time to fly from Sydney to Chicago O'Hare International?

The cheapest month to fly from Sydney to Chicago O'Hare International is usually October.

Which upcoming date is cheapest to fly from Sydney Airport to Chicago O'Hare International Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago O'Hare International Airport on Monday, 5 October 2026.

Can I get a direct flight from Sydney Airport to Chicago O'Hare International Airport?

No airlines currently offer direct flights between Sydney Airport and Chicago O'Hare International Airport. Most routes have one or more stops.

How can I find the best flight deal to Chicago O'Hare International?

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 O'Hare International 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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Sydney Airport to Chicago O'Hare International with?

Currently, Air Canada offers the cheapest flight tickets to Chicago O'Hare International.

Flying from Sydney Airport (SYD) to Chicago O'Hare International Airport (ORD): what you need to know

Chicago is 17 hours behind Sydney and observes the UTC-6 timezone.
Your SYD to ORD flight won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.
Travelling during a peak month like July? Public holidays and other popular seasons can lead to longer lines at airport checkpoints. Play things extra safe and get there up to four hours before an international flight and two hours before domestic departures.
Consider adding a stopover when booking your ticket from Sydney Airport to Chicago O'Hare International Airport. Just uncheck 'Direct flights only' to break up your trip, or even explore someplace new along the way. Here are some options between SYD and ORD:
- Dallas Fort Worth International Airport
- Los Angeles International Airport
- San Francisco International Airport

How to find the cheapest flights from Sydney Airport (SYD) to Chicago O'Hare International Airport (ORD)

$1,279 is the best price for a one-way Sydney Airport to Chicago O'Hare International Airport flight. A return flight starts at $1,719. These prices may change depending on demand.
Don't leave things to the last moment. You're more likely to find cheap tickets from SYD to ORD if you book ahead. Airlines often have some amazing early bird deals.
Finding cheap flights from Sydney Airport to Chicago O'Hare International Airport is easier if you're flexible with your travel dates. Use the 'Whole month' function to see the best prices across each month and land a great deal.
Finding cheap flights from SYD to ORD is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as fares go down.
Lock in the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Sydney Airport to Chicago O'Hare International Airport, use the 'Sort by' function. You can also filter by airline, departure and arrival times, and number of stops.

Handy information about Sydney Airport (SYD)

66% of flights that leave from Sydney Airport land at their destination on time.
Sydney Airport is around 8 kilometres from central Sydney. If you're driving, ride-sharing or catching a taxi from the centre, it'll take you 20 minutes or so to get there, depending on the traffic.
You can expect a journey time of roughly 15 minutes on public transport.
Searching for a convenient hotel near SYD? If you've booked an early flight from Sydney Airport to Chicago O'Hare International Airport, these accommodation options will put you moments from your departure gate:

Arriving at Chicago O'Hare International Airport (ORD)

If you're getting in on a late Sydney Airport to Chicago O'Hare International Airport flight, few things top the convenience of staying close to the terminal. Grab your luggage from the carousel and then be resting soon after at one of these accommodation options near ORD:
Pick up a Chicago O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are well-known companies you can book with here.
Booking your vehicle from Chicago O'Hare International Airport about four weeks ahead increases your chances of getting a good deal.

When to fly to Chicago O'Hare International Airport (ORD)

It's time to pick your dates for your flight from Sydney Airport to Chicago O'Hare International Airport. July is the most popular month to head to Chicago. If you like a more low-key vibe, go in March.
When booking your flight from Sydney Airport to Chicago O'Hare International Airport, think about the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 16ºC to 28ºC.
If you'd rather travel in cooler conditions, look for a cheap ticket from SYD to ORD in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of the United States

Chicago has loads to offer, but there are so many other parts of the United States you'll want to see. About 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the go. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
Indianapolis is another must-experience destination in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.