Flights from Sydney (SYD) to Chicago (MDW)

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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
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

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 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 and rising to 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 )
  • 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

Hotel Chicago West Loop
Hotel Chicago West Loop
2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
The price is AU$195 per night from 1 Jan to 2 Jan
AU$195
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
8/10 Very Good! (1,000 reviews)
"Staff was nice, though the parking was ridiculous. Got there and couldn't even purchase aspit to park car, were sold out."

Reviewed on 20 Dec. 2024

Hotel Chicago West Loop
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is AU$175 per night from 2 Jan to 3 Jan
AU$175
includes taxes & fees
2 Jan - 3 Jan 2025
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,299 reviews)
"Staff was great,location was beautiful"

Reviewed on 28 Dec. 2024

Congress Plaza Hotel
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
The price is AU$127 per night from 5 Jan to 6 Jan
AU$127
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,523 reviews)
"Enjoyed the stay"

Reviewed on 27 Dec. 2024

Best Western Grant Park Hotel
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.