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.

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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$2,182
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time zone:
America/Chicago
Address:
Sydney NSW,
Australia
IATA code:
SYD
Longitude:
151.179898
Latitude:
-33.932922
Time zone:
Australia/Sydney

Sydney to Chicago Flight Deals from AU$2,182

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$2,182 and rising to AU$4,478 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 June)
  • 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

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is AU$232 per night from 4 May to 5 May
AU$232
includes taxes & fees
4 May - 5 May
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,004 reviews)
"Close to Whole Foods grocery. I didn’t like our room which was the last corner room to the freeway noise."

Reviewed on 22 Apr. 2025

Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is AU$245 per night from 30 Apr to 1 May
AU$245
includes taxes & fees
30 Apr - 1 May
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
Nice but could be better
"The room was prettt clean but there were several dusty areas. The beds were not comfortable and very low to the ground. The sofa sleeper was only comfortable if you slept on top of a comforter."

Reviewed on 20 Apr. 2025

Sonder South Wabash
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is AU$256 per night from 4 May to 5 May
AU$256
includes taxes & fees
4 May - 5 May
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,000 reviews)
"We had a great time on this hotel!!"

Reviewed on 21 Apr. 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^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.