Cheap flights from Sydney (SYD) to Chicago (MDW)

Plan, book, fly with confidence

Be in the know
Get alerts if flight prices drop or rise*
Book smarter
Save up to 30% on select hotels after you book a flight*
Earn twice
Earn your airline miles on top of our rewards
Sign in

Flight from Sydney to Chicago (SYD - MDW) route information
Origin airport	Kingsford Smith Intl.
Destination airport	Midway Intl.
Distance	14785 km

Sydney to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Sydney to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from SYD to MDW and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Sydney to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from SYD to MDW. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Sydney Airport to Midway Intl. Airport (MDW)?

Round-trip journeys between Mascot Airport and Midway Intl. Airport (MDW) start from . This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year — book today so you don’t miss out. Prices and availability are subject to change. Additional terms apply.

Do I need to pay a cancellation fee if I cancel my flight from Sydney Airport to Midway Airport?

Most flights can be conveniently canceled online, but whether you are charged a fee depends on your airline. If you do need to cancel your vacation, follow the easy instructions in the Customer Service Portal.

How do I find cheap flights from Sydney Airport to Midway Intl. Airport (MDW) that have flexible change policies?

Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Sydney Airport to Midway Airport flights, you’ll see a “no change fees” filter for you to select.

How far is the flight from SYD to Midway Airport?

With around 14,900 kilometers separating Sydney Airport and Chicago Airport, your flight will be a long one. Pack wisely to make your trip comfortable. Simple things like warm clothing and some noise-canceling headphones should be in your hand luggage.

Which airlines fly direct from SYD to Chicago Airport?

You won’t find any airlines operating directly between Mascot Airport and Chicago Airport, so be ready to make at least one stop on your journey. A layover, whether short or long, can be a nice way to break up a trip!

Are Sydney Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute?

Booking your trip from Kingsford Smith Intl. Airport (SYD) to MDW last minute could save you some serious cash. However, it might cost you a whole lot more! If you’d rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.