Flights from Sydney (SYD) to Chicago (MDW)

Considering a quick trip to Chicago, but not sure which is the best route for you? Well, you’re in luck! Wotif has done the hard work, so all you need to do is check out these flights from SYD to MDW. With heaps of cheap fares from Sydney, we guarantee you’ll be arriving to your holiday destination in style without emptying your bank account in the process.

It’s easy to book flights to Chicago from Sydney  

For a huge choice of flights, simply enter your travel dates and hit search and we’ll hunt out fantastic deals on one-way, return and multi-city airfares to Chicago from Sydney from 10 different airlines. If you click the ‘direct flights’ box, you see flights that’ll get you to Chicago in just hour(s) and mins, too.   

Snap up great deals on flights to Chicago from Sydney 

Choose from flights a day on average, with prices starting at AU$8,136 and rising to AU$8,282 depending on the cabin class, travel dates, and airline carrier. And if you’re up for a last-minute getaway, you can get great deals on flights from Sydney to Chicago today!  

Find cheap airfares to Chicago from Sydney 

Here are our insider tips for bagging a flight bargain: 

• Look for midweek flights and late night, early morning arrival and departure times
• Check out other airports near Sydney and Chicago
• Avoid peak season (prices tend to be lower in April)
• Be flexible with your travel dates and you can usually get cheaper options  

Reasons to book your flights to Chicago from Sydney with Wotif

Wotif is a super-easy way to find the best flight for you to Chicago. Get more bang for your buck on flight and hotel or car rental combos and download the free Wotif app to tap into exclusive deals. Book now with Wotif and have a great flight!