Flights from Sydney (SYD) to Chicago (MDW)
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Cheapest Flights from Sydney (SYD) to Chicago (MDW)
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.
Best Day to Book Flight from Sydney (SYD) to Chicago (MDW)
Sydney to Chicago Flight Information
Find the Cheapest Flights from Sydney (SYD) to Chicago (MDW)
Work hard, travel harder! Wotif brings you the cheapest Sydney to Chicago flights, making it possible to have a five star holiday without that five star price tag. Browse and compare our top SYD to MDW routes and airport options. So, go ahead and treat yourself, your sweetheart, or the kids to an unforgettable holiday this year.
to Information
Traveling From | Kingsford Smith Intl. |
|---|---|
Origin Airport | |
Origin Airport IATA Code | SYD |
Traveling To | Midway Intl. |
Destination Airport | |
Destination Airport IATA Code | MDW |
Number of Airlines Serving | |
Average Flight Time | hours mins |
Direct Flight Time | hours mins |
Flight Price | AU$2,556 |
Top Airlines Servicing SYD, Kingsford Smith Intl. Airport
Top Airlines Servicing MDW, Midway Intl. Airport
Sydney to Chicago Flight Deals from AU$2,556
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$2,556 and rising to AU$2,892 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 May)
- 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!
Great places to stay after flight from Sydney to Chicago
Reviewed on 8 May 2025
Reviewed on 9 May 2025
Reviewed on 12 May 2025
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^Savings based on all package bookings made with Flight + Hotel on Wotif.com from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.